The user wants me to translate a Chinese title into English. Let me analyze this: "两万字产品销售深度干货：Clari CRO 揭秘 4 万亿收入管理背后，驱动销售增长的独家法则｜Z Talk" Breaking it down: - 两万字 = 20,000 words - 产品销售深度干货 = in-depth product sales干货 (干货 is a Chinese internet slang for substantive/practical content, often translated as "insights," "know-how," "practical guide," "deep dive," etc.) - Clari CRO = Clari CRO (keep as is, it's a company title) - 揭秘 = reveals / unveils / breaks down - 4 万亿 = $4 trillion (or 4 trillion - need to decide if currency is implied; in Chinese business context this is likely USD or just a number; given Clari is a US company, probably USD) - 收入管理 = revenue management - 背后 = behind / under the hood / behind the scenes - 驱动销售增长的独家法则 = exclusive rules/principles for driving sales growth - Z Talk = Z Talk (keep as is, likely a publication/series name) This appears to be an article title for elsewhere.news. Let me craft a natural English headline. Options: - "20,000 Words of Deep Product Sales Know-How: Clari CRO Reveals the Exclusive Principles Driving Sales Growth Behind $4 Tr
As a salesperson, my job is to understand all the internal constraints within the client's organization.
Z Talk is ZhenFund's column for sharing insights.
Founded in 2012, Clari is an AI-powered revenue platform that offers revenue operations, sales engagement, and conversation intelligence services. Currently, Clari manages $4 trillion in revenue for over 1,500 clients, including well-known companies like Zoom and Adobe. Previously, Clari raised $225 million in its Series F round at a valuation exceeding $2.6 billion.
Ben Fiechtner is currently President of Americas at UiPath. He was formerly Chief Revenue Officer at Clari, responsible for global go-to-market and revenue operations, and also served as Senior Vice President at UiPath, successfully growing the company's revenue from $150 million to $450 million in key accounts and regulated industries. Before joining UiPath, he held multiple senior roles at Salesforce and was at the forefront of vertical industry sales.
In a recent in-depth interview, Ben explored how to communicate effectively throughout the sales process, the keys to closing deals, and how to hire top salespeople and design compensation incentives.
ZhenFund actively tracks frontier technology and innovation trends. Going forward, we will continue bringing you insights and deep thinking from the world's top entrepreneurs. Stay tuned. This content comes from the 20VC podcast; below is the full translated transcript.
Key Takeaways
- The key to opening negotiations with clients: Truly dig deep into the client's business and show up with a strong point of view at the executive level: "This is the direction I think you should move in, and here's how I can help you get there."
- The salesperson's job is to understand the client's constraints: Continuously offer options and ask the right questions to figure out what those constraints are. Truly understanding how the client's budget relates to OpEx, CapEx, cash flow, and so on lets you understand what levers are available inside the organization.
- The 4C Framework for optimizing revenue: Always focus on four aspects of the business: Create, Convert, Close, and Churn.
- Verticalization of product and marketing is the future trend: To enter verticalized markets, you need to learn to speak the customer's language and truly understand their sales logic.
01
After Landing My First Big T-Shirt Order,
I Gave Up on My Dream of Becoming a Lawyer
Harry Stebbings: Ben, I'm so excited. I've heard so many incredible and entertaining things about you from mutual friends. Thank you for agreeing to this interview.
Ben Fiechtner: I'm thrilled to be here too, though also a bit nervous, because I know you've probably heard quite a few stories.
Harry Stebbings: This isn't your first time in the public eye, because you first gained widespread attention when you were a young entrepreneur—you started a T-shirt company. As a starting point for this interview, tell me about this college T-shirt business.
Ben Fiechtner: My roommate Troy Vossller and I were both nerds in high school. Freshman year, we made a lot of T-shirts for sporting events, student government, things like that. It was a time when almost every rapper was starting to sell clothes.
We were like two kids who'd had one or two adult beverages on a Wednesday night, and we said, "We should start a T-shirt company."
There was this term "Sconnie"—it was like what "Cheesehead" means for Wisconsin. It represented pride in everything Wisconsin: cheese curds, drinking PBR while driving John Deere tractors.
We trademarked the word and started selling T-shirts. We each put in $300 and sold out in about two days. We thought, wow, we've found something here. So we built an e-commerce site, started doing wholesale, and everything just aligned. Troy still runs the company, and it's doing very well.
Harry Stebbings: Wow, I had no idea it was this successful. I assumed it would have folded like so many others. So it's still operating, and Troy's still running it.
Ben Fiechtner: Yeah, a lot happened, and I think it was the most incredible experience for both Troy and me. I'd wanted to go into politics, become a lawyer or something.
When we landed our first big order with the University of Wisconsin bookstore, that was the moment I thought, wow, I love sales, this is so me. That's how I got into sales.
Second, throughout our four years of college, our company achieved tremendous success in terms of recognition and brand. Our wholesaler, who was also our friend, handled all the inventory and shipping for us. So we just took a small cut, did very little in brand building and guerrilla marketing, and it was all incredibly fun.
Harry Stebbings: I'm almost embarrassed now. I didn't realize it was this successful. Did you keep your equity?
Ben Fiechtner: He bought me out, I forget what year. We're still friends to this day. He owns everything now, and I'm more of a figurehead owner.
Harry Stebbings: That's amazing. You mentioned your love of sales, which started with that first big order. What specifically did you love about sales?
Ben Fiechtner: I'd wanted to go into politics, become a lawyer. I don't know, I was dumb and young, and I actually found the lawyer with the biggest ad in the Yellow Pages and asked him to dinner. I took him to the most expensive steakhouse in town because I knew he'd pay. Though I did offer to cover it.
He asked me, "Ben, how many T-shirts did you sell tonight?" I said, "Five." He asked, "How much did you make?" I said, "$72." He said, I have to go back to the office, work long hours to make more than that, and you've already found a shortcut. That kind of shifted my direction.
I realized I wanted to pursue this career not because I loved arguing, but because I loved sharing my point of view. I loved helping people see what they weren't seeing. That's what debate, politics, and law all offered me.
But when we closed that first deal with the university bookstore, it was kind of like helping them see a market that had never existed for them. For a long time, they hadn't changed their designs, hadn't done any marketing, hadn't communicated what students actually cared about—they'd been using the same prints for 100 years.
And convincing them to adopt my perspective, to succeed with it, was incredibly fun to me. That adrenaline rush, that feeling of hunting prey, got me hooked. I knew I was going to be in sales.
02
A Salesperson's Job Is to Understand
All the Constraints Inside the Client's Organization
Harry Stebbings: That's so interesting. I share many of those abilities you mentioned, and one of them is drawing out what clients want, helping them understand your perspective and persuading them.
On the point of getting clients to understand your perspective, what's your most important lesson? What questions do you ask? What works? What doesn't? How do you do it?
Ben Fiechtner: Most organizations I've joined have been in mature stages, and a lot of tech companies have become product sellers. They talk about themselves, about product features and functions and all kinds of details.
I think the first thing is, you're not persuading someone to understand an existing point of view—you have to show up with your own.
Just like when you go to your boss, you can't say, "Hey, I have a problem." You have to say, "I have a problem, and here's what I think we should do about it."
Similarly, when you're talking to a client, I think we should teach salespeople to truly study the client's business—this is the easiest thing to do.
If you show up with a strong point of view, like: "Hey, I've talked to your team, and both qualitative and quantitative research show that this is the direction I think you should move in, and I can help you achieve that goal through this path."
It may not work every time, but you'll likely have a much better chance of earning a seat at the table and actually participating in solving the client's business problems.
Frankly, I've bought enough software from people who didn't understand my business and had no particular methodology for solving my problems. None of it solved my problems. We're no longer in an era where we buy technology just for technology's sake.
So, regarding how to truly open negotiations and discussions with clients—yes, you'll ask a lot of questions, do all the right things, but most importantly, before engaging with someone, you have to do your homework first, then show up with an executive-level point of view.
Harry Stebbings: Some people say one of your superpowers is creativity in closing deals. They say you're one of the best in the world at getting deals across the finish line, and you bring your GTM team along to develop that capability. What makes you so exceptional at closing?
Ben Fiechtner: I don't know who taught me this, but I think at Salesforce there were many great mentors who had been instilling this in me for a long time.
There was this big boss Eric who once told me, "You own the pricing."
I said, "I can't own it, I have to go through all these approvals. I have to ask this person and that person, and ultimately you're the one who approves it." He said, "No, you own the pricing."
So this idea was planted in me very early: as a salesperson, my job is to understand all of the client's constraints.
These relate to their OpEx, CapEx, cash flow—whatever it might be, and it's usually very difficult to figure out. Because sometimes the buyer knows this information, sometimes procurement knows it, and sometimes it's someone in finance you've never even spoken to.
But by continuously offering options and asking the right questions to figure out their constraints, you can truly understand what levers you have available inside that company.
This ability comes from years of training with many great mentors. For example, how to find balance between your constraints and their constraints and arrive at a win-win situation.
But too often people just say, "Here's my pricing. Here's my discount percentage. Are you buying or not?" without truly understanding how budget relates to OpEx, CapEx, cash flow, and so on.
Harry Stebbings: What questions would you ask to figure this out? Let's say I'm a great product founder, but I don't know any of this stuff. I want to run sales myself before hiring my first rep. What should I be asking?
Ben Fiechtner: What I've always done — and this depends on whether you're on a per-seat model or a consumption-based model — is: how do you want to buy?
I'm not going to force you to buy this many seats or this much stuff. We just need to understand what you're trying to achieve, how you want to land, and then work backwards.
Once you build that landing plan, based on when users need to go live, typically aligned with normal business requirements. You also need to consider the trade-off between business lift and implementation complexity. Show that plan to the customer, work together through execution, and keep adjusting.
Second thing: start date, commercial terms, contract length — these are the biggest levers in traditional SaaS, and I'll tell you that right away. Where do you have flexibility? Let's combine those.
A big part of it is understanding what they want to achieve, then understanding what levers you have internally, and bringing those two together.
Harry Stebbings: Which levers are you most willing to compromise on?
Ben Fiechtner: Without giving away too many secrets about how to negotiate with Clari, I think what we care most about is seat count.
The more seats you have, the lower your price goes. That's true for every per-seat pricing company. Same with consumption-based pricing. The more you commit, the better your price.
Next for us is start date. How quickly can you get the customer live? SaaS companies can't recognize revenue until users are actually activated. So if you don't activate for six months, then I'm waiting until Q4. In that sense, a Q2 deal is worth more to me.
Third is contract length. Fourth might be some simple terms and conditions stuff, like payment terms and so on.
03
CFOs Aren't Spending Less
They're Just Spending Differently
Harry Stebbings: What about pricing? How do you think about discounts? Some people use it as a weapon, some don't — it's interesting.
Ben Fiechtner: It depends a lot on the maturity of your sales team, and you have to set guardrails. For governance, to make sure nobody does anything stupid.
But one thing I actually did: I told salespeople at my last three companies, "You own pricing."
If you come to me and explain clearly why this pricing is important for customer success, and keep it within reason, we'll give you the pricing you need.
Even more so now, in the current macro environment, with SaaS in a downturn, we have to focus on long-term success. People talk about getting creative with deals. We've started customers at extremely low pricing because they were tight on cash. But we knew it would be a long-term contract, and it would help them.
We've done unconventional things. If we know enough and the customer is willing to share their constraints, we can always find a way to solve it.
Harry Stebbings: Is there any way to create urgency in a deal? That's another thing I find really challenging. I'm on the board of a lot of companies, and they often say they can't create urgency in the sales cycle. What would you advise?
Ben Fiechtner: I think beyond the traditional "let's drive something with massive impact," you can work backwards to find something that uniquely solves a problem for them. It's an urgent problem to solve, and obviously that's the easiest way to create urgency.
Uncover what the key decision-maker (the economic buyer) needs to succeed, understand their success criteria, and support them through building good relationships, storytelling, or whatever it takes to move the project forward quickly — be in the boat with them.
A lot of the time, don't go looking for personal relationships or anything like that. If someone feels resonance with you, feels that your solution is connected to the success of the product and the project, they'll also be urgent about getting the deal done. That's probably the most successful method, outside of what we traditionally do.
Harry Stebbings: Do you look for multiple decision-makers in the sales process? And if so, how do you do it? I've always found this hard. Will you introduce me to your team? Because you might get hit by a bus and not be there, and in that case, I still want to close this deal.
Ben Fiechtner: Yeah. I think when I was a salesperson, what I was trying to do was break down the human suspicion or barrier between people. I would just be upfront: "You know I'm a salesperson, this is my job."
For me now, to some extent I'm helping salespeople, so I can easily say to a CRO: you're in the same position as me, you know, I also have to talk to the CFO. I have to make sure I understand his or her constraints to solve this problem.
I think I did the same thing when I was in sales. A lot of it was just trying to make it a human element. If you act like a stereotypical salesperson and say, "Harry, I really..." and make up some bullshit reason for why you need to meet someone, they'll see right through it.
Honestly, the only thing that matters at that point is authenticity. So what I've always done is just be straightforward: "I'm a salesperson. My job is to think about this from every angle and close the deal. So I'm not going to waste my team's time, and I'm not going to waste your team's time. Can I get introduced to X, Y, or Z?" It works 90% of the time.
Harry Stebbings: Anything you should or shouldn't do on payment terms and conditions? Anything where you're like, "Hmm, I learned to be careful about that"?
Ben Fiechtner: I think pushing out payments for a long time because someone's in a tight cash position — that usually doesn't end well. You have to be very smart about making those kinds of bets.
I've done it. I knew the customer was tight on cash, felt for them, wanted to keep them around. But those really have to be done very carefully, and now I would be cautious.
I think cash has become exceptionally important, especially with rates where they are. People are tightening those risk windows, and that's becoming standard across the industry. So overall, there's less give and take in negotiations.
Harry Stebbings: Do you think buying new technology is slowing down? Like people say CFOs are tightening budgets, decisions are getting more centralized.
Ben Fiechtner: It's interesting. Most CFOs I've talked to say, "We're spending the same, we're just spending it in different places."
I think what that means is enterprise technology is consolidating. So they're trying to say, "Hey, can I leverage one platform as much as possible? I don't need 12 best-of-breed products."
People are obviously experimenting with generative AI right now — we almost have to mention it 10 times on every podcast. You'll see people shifting spend to AI, spending more on AI, and it can be very expensive in some places.
But I don't think people are buying less. They're just buying differently, and I think right now there's more buying of technology platforms — platforms that have proven success — rather than just shiny objects.
So if you can show substantive improvement on ROI, cost savings, revenue growth — whatever the customer cares about — you can get the deal done. But if you're just offering a shiny object, yeah, you're going to get cut.
The 4Cs of Sales Growth
"Create, Convert, Close, Churn"
Harry Stebbings: What about forecasting? This is your specialty. In this world, how do you forecast with precision? You know, the fun of traditional SaaS was every seat renews and your revenue goes up 20%, great business. But now forecasting is so hard to control. If I'm a founder, how do I forecast accurately in volatile times?
Ben Fiechtner: I think there are three things.
First, how do you drive the simplest process? I always tell people, salespeople aren't lazy, they're just looking for the fastest path from point A to point B, so you have to make it super simple, super direct.
Second, what I've learned in this role is that process really matters. I've sat in a lot of forecast calls, and I meet with a lot of CROs. In these forecast calls, you'll hear them say: "Hey, this deal is still good."
But at UiPath and Clari, we manage a 13-week revenue cycle and break it into four different phases. In week one, the team is all looking at the same things: slipped deal reviews, pipeline progression, commits. This ensures all the team members and frontline managers know what's happening.
And you as an executive have the opportunity, through exception-based management, to identify and solve problems in the business — like "Where are the holes in my business? Is it top of funnel? Is it conversion? Is it execution? Or is it churn and retention?" That process is about finding where to make adjustments.
So simply put, in this 13-week quarter management: first, tools matter; second, process matters.
Harry Stebbings: I want to go deep on these different phases of the 13 weeks and how you execute it. Break it down for me. What do we do in week one?
Ben Fiechtner: Week one of a quarter, I typically look at slipped deals, because that's the most direct path to revenue that was supposed to already come in. It's not that I'm blaming anyone, I'm just doing more homework on where I can get data.
Harry Stebbings: What are good reasons versus bad reasons for a slipped deal?
Ben Fiechtner: Weird stuff happens all the time. I think for me, a good reason is: we were trying to move fast, so we hadn't completed all the necessary steps. This deal really should have been in Q2, not Q1. That's my favorite reason, because things just happen or move around.
Sales is the only profession where you try to control everything, and yet stuff still happens. So you control what you can control. I can't say there's a good reason for a slipped deal, just less bad reasons.
Harry Stebbings: Okay, so that's point one, like analysis of slipped deals. What's point two?
Ben Fiechtner: Like most companies would say: "Hey, reps, write down what you're going to commit to this quarter."
The next best practice is that we line up our forecast number against actual deals or contracts in place. So if I'm committing to $1 million, I'd better have $1 million in committed deals.
First, you're calculating a number, but second, you're also judging which deals are closest to closing.
Harry Stebbings: Leaders always ask for more, admit it, Ben.
Ben Fiechtner: Yes, they ask for more, but I think this is week one, it's early, you haven't done your QBR yet. I want that number to at least match. Of course I want the pipeline opportunity and expected value to be higher than what's committed, and all the channels to perform better than the best-case scenario.
But I think in week one, you should be more realistic. Because in many organizations I've been in, often they can't actually support the forecast with deals that are already done.
Harry Stebbings: But just like our leaders ask for more, when you say "I can do 1.2 of the plan," I'll say, "Come on Ben, I want to do 1.4." Am I wrong to say that?
Ben Fiechtner: I think the best leaders don't believe the story that's being told at every quarterly business review. At every QBR I've been to, every rep puts up a slide that says, "I hit 120% of plan." Every single time. But can you really hit 120% of plan? You can't.
From the best sales executives I've been around, what I've learned most is, yes, you push them to say more, but you also have to be brutally honest about the true state of the business. And that takes a 13-week process of inspecting and understanding the holes in your business.
Harry Stebbings: So point two, we need to get the leader to write down their forecast number. What's point three? That last one was so good.
Ben Fiechtner: Point three is also something we focus on in week one, where we look at renewals for that stage after a quarter has passed. We've found it takes about three to six months to make meaningful changes to renewals, whether that's retention, churn, or expansion. So we're actually looking at this on the dashboard in week one of the new quarter.
Harry Stebbings: What does that involve?
Ben Fiechtner: For us, the way you look at it depends on the specific business, but you might be monitoring your adoption and usage data.
You certainly know when contract dollars are coming due and need to be renewed, and you cross-reference those two things and say: "Hey, if this customer doesn't have great usage data, adoption isn't high, but it's a big contract, then we prioritize this customer."
Harry Stebbings: Prioritize meaning, we send more CSMs over, or we give them more attention? What do we do?
Ben Fiechtner: In week one we might do a lot of work around this customer. But for me it's simple: "Hey, let me look at this quarter, do we have any obvious renewal risk?"
This might only be 5% of the forecast call, but at the start of a new quarter, let's set up a call to discuss potential renewal risk, or prepare the team in whatever way you can think of. Because if our top 10 renewal contracts are at risk, we should deal with it immediately, not 90 days from now.
Then step four is basic: let me look at the overall pipeline. When evaluating pipeline, you need to reference historical conversion rates at different stages.
I think this is where our tools come into play, where forecasting and machine learning results tell you, based on the current stage of the pipeline — early stage, mid stage, late stage — to predict future sales outcomes.
Once you have these four things, in week one we can run through the whole thing. But after that it becomes more about checking pipeline conversion rates and so on. In the final weeks it's pure execution, confirming whether we're doing the right things to drive the business forward in the shortest possible time.
Harry Stebbings: Such a nuanced explanation, many founders will probably be taking notes word for word.
My question is, should we continue talking about week two? Or do you feel there are certain nodes that make good milestones?
Ben Fiechtner: We broke it into four big buckets. This is something I documented with our SVP of Revenue Operations.
We felt these insights should also be available to customers, and often we send them to them, or do back-analysis based on their respective business needs or revenue targets.
Each week's dashboard has different controls, different sections, but ultimately you're looking at four aspects of the business.
I use a cheesy alliteration to make it more digestible, we call it "Create," "Convert," "Close," and "Churn," and depending on the week, your depth of focus on each varies.
So you can imagine, "Create" is the most important part of week one, which is looking at the overall pipeline: "Do I have enough pipeline? What's my historical pipeline coverage? Same time last quarter, same time last year, what's my pipeline at different stages?" These are the things you really want to understand about the business.
And by week six we're in "Convert," where I look at stalled pipeline, deals that have been sitting at a stage for a certain amount of time. For example, in the MEDDICC framework, where do I have gaps?
"Close" is the focus of the final three weeks. Just make sure which deals are committed but haven't discussed budget, haven't signed the MSA, haven't exchanged documents, haven't met with key stakeholders or sponsors, whatever it is.
And finally "Churn," the scary "C," which the business needs to always keep an eye on. In software, I can't do something unnatural to get you to renew in less than 3-6 months, so we're always looking at next quarter, the quarter after, and looking further out depending on the week, giving ourselves more time to really intelligently see what's coming.
Harry Stebbings: What's at the core of doing "Convert" well?
Ben Fiechtner: First, you use all the data to show where deals are stalled. Some of it might be CRM issues, might be lack of operational rigor. We use the MEDDICC framework internally to make sure we're asking the right questions on forecast calls.
Interestingly, all my leaders now record their forecast calls, and I listen to smart summaries on Sunday nights instead of going to forecast calls and asking, "Hey, are we still moving that deal forward?"
This way, I know my VP of Enterprise's number, and that three of her five biggest deals are at risk. Then I specifically study why these three deals are stalled — maybe it's legal, maybe it's security, maybe we haven't built relationships with the people who can move the deal forward.
But I think, once you've aggregated this "Convert" content for most of the quarter and at key mid-quarter points, you become absolutely focused on the holes in these deals, not on blaming team members.
The focus is, how do we use the power of the company to help them get this deal done.
Harry Stebbings: What tools and processes do you use in the "Convert" stage to push deals forward?
Ben Fiechtner: For me, as CRO, there's a gun to your head every day, you don't have enough time. So all I need is a clear signal telling me where there are gaps in the business.
And often, the gaps are in "Create" or "Convert." So if I go into "Convert," I can look at call recordings, sales interactions, I can look at MEDDICC questions, I can do deep deal reviews and say, "Hey, these deals aren't progressing or are at risk." Clari will tell me, "Look, these five deals won't close," and then I know where to start.
As a sales leader, your job becomes very natural. I think for most people, it's about understanding deal progress, offering help, and moving on. So, from tools to process is about making sure things don't fall through the cracks.
But ultimately, it's just about trying to get your time spent on what matters, not on irrelevant details.
The Biggest Reason Deals Don't Close: Not Understanding the Customer's Buying Process
Harry Stebbings: How do you advise founders to use teamwork to get a deal done? What do you do in these situations?
Ben Fiechtner: I think if the team isn't already a well-functioning team, it's hard to make it work well together on a deal.
Building good cross-functional relationships is the foundation of everything. My job as CRO is to work closely with product, marketing, the CEO, and have open and honest relationships.
So talking to them shouldn't be, "Hey, this is the special thing I need from you for this deal with Harry." It should be more natural, more everyday, where you can directly say, "Hey, this might need a product roadmap, this might need some marketing boost," and so on.
If you haven't built that trust and foundation upfront, it becomes very difficult.
There's a joke that when certain sales teams show up with 16 people in the room, it shows they lack necessary preparation. And teams that show up with just three people are usually well-prepared, support each other, and flex roles.
So I think, my job as CRO is like glue, presenting consistency when working with customers, to make sure we're on a unified front.
Harry Stebbings: I join a lot of boards. They'll say, the deal slipped to next quarter. They love us, we have a great relationship, but they'll just say, it slipped to next quarter.
When someone on your team says that, how do you respond?
Ben Fiechtner: I hope at that moment, you already understand who the decision-maker is, what their decision criteria are, what are the compelling events that drive the decision-maker to act? Is this budgeted and appropriated? These are some traditional MEDDICC questions.
Through a brief one-on-one with the salesperson, you can pretty quickly tell whether they've actually done the work, or whether they're just believing their friend inside the customer. They do have a good relationship, but it's not actually helping them drive the sale internally.
I believe every sales methodology exists for a reason. If you're doing the homework eight out of nine times, it's going to work. It's largely about doing the right research, asking the right questions, and you won't go wrong.
Harry Stebbings: What's the biggest reason deals don't close?
Ben Fiechtner: Quite frankly, it's that you don't understand the customer's procurement process. I say that because the deals that typically don't close are the ones that have been committed — those are the most painful. Like, we have a 75% chance of being selected, we're the preferred vendor, and then the deal doesn't happen. It's really just a process issue. You haven't truly understood what the customer has to do internally for us.
Harry Stebbings: What about churn? The hardest part is the relationship between customer success and sales. We close three deals, then lose four. Usually it's because I closed the deal and handed it over to customer success like a bad relay.
How do we build good interaction between sales and customer success to make sure our software implementation and adoption go well?
Ben Fiechtner: Going back to your earlier question. It's largely about how you sell. So you have to sell in the right way, thinking about the structure of the deal, thinking about when the customer wants to start using the product, truly understanding that process. And not just saying, "This is a great little widget, buy it."
Planning the customer journey based on business value and implementation complexity — understanding before the sale what the customer is going to do and what they need to do — makes it much easier to hand that plan over to customer success.
Let them take it like they've been involved all along. If you're just saying, "Hey Harry, I have a great product that solves all these problems," but you haven't actually done thorough selling, then no matter how good your customer success team is, it's not going to work.
You need a very thorough, outcome-based sale from the very beginning to ensure your customer success team can be successful.
You Have to Find Your Product's Segment
Harry Stebbings: I'd love to discuss the bigger journey of moving from small commercial agreements to enterprise agreements. What's your biggest lesson learned in going from small customers to large enterprise customers?
Ben Fiechtner: I was fortunate to start my career as a commercial account executive at Salesforce, and then had the good fortune to join the enterprise team as a global account executive, so I got to observe that transition from small commercial to enterprise. It was interesting. I was talking to the AVP, and he said, "Ben, you have to treat this customer like 80 small customers."
It's a large global enterprise group, they have different P&Ls, different regions — if you treat them all like small commercial accounts, do your homework for each one, solve their individual problems, then one day you'll facilitate a large enterprise agreement.
For me, the essence is the same. It's just the number of internal stakeholders and the number of people you need to help you get things done that's different. Of course, external stakeholders too. Selling to a 300,000-person company is much more complex than selling to a 300-person company.
But I think for the best companies in the world, the process and actions behind it should be the same.
Harry Stebbings: But can the process and actions really be the same? You're the CRO — resource allocation is one of your core responsibilities. You can't allocate the same resources to a $5,000 ACV customer as a $500,000 ACV customer.
What's your view on this, and in a PLG world where customers often enter through small trials or low-cost entry, does this become even more challenging?
Ben Fiechtner: That makes complete sense, but I'm referring not just to the actions or process of selling. I hope I'm engaged in solution selling.
I deeply understand the customer's problems, provide my perspective and recommendations, show them how I uniquely solve their problems, I do creative deal structuring, and ultimately make it a win-win.
For long-tail, smaller opportunities, consider building self-service models to reduce selling costs and management complexity.
But given the complexity of internal and external stakeholders, you need more people, more capability, and higher output on your largest customers. I think that's common most places.
And how should we think about it? I think it's like trial and error.
I've seen it many times — like your favorite salesperson or the person who cries the loudest gets more resources. Yes, the squeaky wheel gets the grease, right? But sometimes you believe them, sometimes you don't.
I think there are a million different ideas about how we properly allocate these resources, and it's largely about iterating through trial and error. And never be too afraid to iterate — to change, especially at a company of our size.
We make decisions based on our observations: where is the buying propensity strongest, where is the biggest opportunity.
But things change, and you have to be willing to iterate and move people around without causing too much disruption.
Harry Stebbings: When do you think is the right time for sales enablement — giving salespeople the resources they need to improve selling outcomes? For PLG founders, when should they start investing in sales enablement?
Ben Fiechtner: I think if you've hired the right sales team, sales enablement shouldn't be an afterthought.
I read an article the other day that said doctors stop listening after 18 seconds. It's not that doctors are bad. It's just that if you talk for more than 18 seconds, people might tune out.
So when you hold these sales enablement meetings saying, "Hey, every Friday there's a mandatory two-hour meeting where we'll talk about product, sales process" — you're going to fall asleep.
If I'm a good frontline leader and I have the authority and responsibility to drive all the micro-moments, we'll tell Harry three things he can do better and help him understand where he can improve.
Really, we need to create a culture that's more focused on accountability and feedback. I've found this drives more effective enablement in micro-moments than large all-hands meetings or weekly syncs.
Especially for startups, where everyone might be in the same office, talking multiple times a day, maybe even eating together.
In that case, I don't think you need formal sales enablement — you just need a very strong sales leader who views accountability and enablement as core parts of their job.
Harry Stebbings: What do you think is the most common mistake startups make when trying to expand from smaller commercial accounts to larger enterprise accounts?
Ben Fiechtner: I think it's a big challenge. At Clari, we compared enterprise accounts to small commercial accounts. We thought, "Hey, we have the most advanced forecasting tool, we should put more energy into enterprise accounts." That was a major strategic decision at the board level.
But many others choose to focus on enterprise accounts because they say, "Hey, there's more money there." That's always true.
But I think you have to find your product's segment, the unique problems your customers face, and how your product solves those problems — that's where you should invest and bet.
I've had friends who say, "We want to be general AI for very small startups, we don't want to deal with the biggest companies in the world. Because we can't build a team that big." I think that's a very smart decision.
Harry Stebbings: Stevie Case, CRO at Vanta, is also on the 20SALES team, and I work closely with her. She always says we can stress-test enterprise in a more reasonable way than people think, without massive investment.
Do you think you can do enterprise on a small scale first, in a way that doesn't require massive company-wide commitment?
Ben Fiechtner: Yes, absolutely I think you can.
But if you're planning to shift your business focus or resources toward enterprise and large customers, you need to be very careful.
Even the biggest tech companies in the world have unique requirements when dealing with other large tech companies.
You're going to have to invest R&D dollars, and many startups and early-stage companies don't have the resources for that kind of large-scale R&D investment.
So I think her point is great — if you're trying to reach out, like "Hey, I'm planning to go after the enterprise market for some big company X, Y, or Z," if that requires a massive shift in your own company's roadmap, you might have to give up some planned development items or features. That's usually the hardest thing for early-stage companies.
Moving Into Vertical Markets
Learn to Speak the Customer's Language
Harry Stebbings: I've found that tighter product marketing and verticalization — focusing on specific industries or market segments — can dramatically improve efficiency and speed. You can build a brand in a much tighter community or market. What's your biggest lesson in building vertical teams?
Ben Fiechtner: On product marketing and messaging, I think Salesforce is an absolute master.
If you just talk about technical details, features, and functionality that aren't connected to the customer's actual problems, you'll fail. Like when we talked to medical device companies, we'd talk about forecasting in terms of "Create, Convert, Close, Churn," and they'd say, "We're actually a consumer products company."
So we had to relearn how to truly talk to medical device companies and truly understand their sales logic. "Oh, okay. You're not doing B2B forecasting like we are — you're forecasting how many syringes you'll use each day or something. How do we adjust to help you track that more accurately?"
So, learning to speak the customer's language, understanding their unique problems, and how you can uniquely solve them. Sometimes you can't solve them — there's a long road there.
For early-stage companies, while going after large customers is attractive, it may not be right for you. So play where you're strong — that's an important lesson I've learned from my last three experiences.
Harry Stebbings: When did you start becoming verticalized? When your product was already quite large? Any lessons on timing?
Ben Fiechtner: We debate this often. I think unless your product is already verticalized for a specific industry, because it does cost money.
I remember a Salesforce executive once telling me, right when we were just starting to break into healthcare, "I actually think you'll shrink this year, and then you'll see exponential growth."
It's an investment. Scaling within a broader scope is much more challenging. So if you're a company of a certain size, you have to accept that.
Harry Stebbings: I don't understand why it would be harder. Product marketing becomes simpler, word of mouth spreads faster, product resonance improves, and you understand your customers more deeply — why would it be slower?
Ben Fiechtner: I wouldn't say it's slower. I'm a huge proponent of verticalization. I think people just say it's more expensive. Because I can't take a banking specialist and drop them into healthcare. Very few people are excellent across different industries or roles.
Your customer success team has to know the space, your sales engineers have to know the space, your account executives have to know it — that requires additional investment.
Plus, you have to specialize your messaging. If you have a broad message, from a product marketing standpoint, it might be a bit easier.
But I very much agree with you. When I talk to other CROs, those who have a sound vertical strategy feel the least pain across macroeconomic environments.
I think companies taking a vertical market approach are in the lead.
Harry Stebbings: Who do you think has the best vertical market sales strategy?
Ben Fiechtner: I want to flip that back to you — you've talked to so many people.
Harry Stebbings: Actually we just invested in a German company called Allo. It's a restaurant payment system provider, competing with LightSpeed and Toast. They have a vertical sales strategy targeting ethnic restaurants. Ethnic restaurants meaning any non-native restaurant, but they staff salespeople from the corresponding ethnicity for each ethnic restaurant, because people prefer to buy from people who look like them.
In countries like Germany, Italy, France, or Spain — when a Chinese person or an Italian person encounters a salesperson who can communicate in their native language, you instantly get a high level of attention.
Ben Fiechtner: That's a really compelling business concept — good eye on the investment. So I think companies with a focused industry strategy and specific industry solutions are performing the best in this macro environment.
Hiring a Great Salesperson
Attitude, Aptitude, and Authenticity Are the Three Most Important Traits
Harry Stebbings: If you hire great people, they can quickly master a specific industry or domain. We've talked about a lot of details, but we skipped an important step — you actually need to hire great people to make all of this work.
How do I hire great salespeople?
Ben Fiechtner: For salespeople, I have a cheesy alliteration: I look at three things — Attitude, Aptitude, and Authenticity — each with slightly different meanings.
I don't care much about experience, and I don't care much about network. I care more about attitude, because in any sales organization you're going to hit problems, and you need to see them as opportunities.
Harry Stebbings: How do you test for attitude?
Ben Fiechtner: I think there are two things. My favorite interview question, which to some degree tests for growth mindset: "Harry, you've had a lot of success. What's the number one reason you haven't had even more success?"
Most salespeople will say, my territory was bad, my quota was too big, my product didn't resonate with customers — say that and you're immediately out.
But if you say, I really didn't work on X, Y, or Z, or I'm working through X, Y, or Z, then I know you probably have a growth mindset, and you have enough self-awareness to know you're not perfect.
Harry Stebbings: What percentage of people attribute it to self-awareness? Versus blaming the segment, pricing, or other factors?
Ben Fiechtner: Surprisingly, probably sixty to seventy percent of salespeople will say something objective that's outside their control.
Harry Stebbings: Okay, that's a quick disqualifier. What else on attitude?
Ben Fiechtner: I think the other side of attitude is how curious they are about the company. Nine times out of ten, I'm not trying to brag or sell, but I'll say, "Hey, here are all the awards we've won."
Then you can quickly tell if they're intimidated by the company, if they want a perfect quota and territory to walk into. The alternative is, they see this as an opportunity, they're willing to face the problems the company has, and believe they can stand out by solving them.
Harry Stebbings: That's very similar to me. When evaluating investment opportunities, I want to see founders demonstrate an entrepreneurial mindset early on, because that has the highest correlation with future success. So I always ask, how did you first make money?
There are two possible answers. One is, "I started selling T-shirts in college — not joking, really did it, learned from it." The other is, "Oh, I graduated from Cambridge and then went to McKinsey." The difference in business acumen between those two answers is massive.
We've talked a lot about attitude. What about aptitude? What are we looking for there?
Ben Fiechtner: Aptitude shows up as intellectual curiosity, and you can see this quickly in interviews too. What surprises me is how many candidates don't ask me questions, or only ask about the next steps in the interview process.
They should recognize the interview is a two-way opportunity. This is your chance to interview me too, right? You're interviewing us as well, making sure you're proactively learning about the company.
Harry Stebbings: What questions should candidates ask?
Ben Fiechtner: I tried this the other day — I asked ChatGPT what the most popular questions are, and surprisingly, a lot of people are asking the same things. So I don't want to answer that.
I think candidates should ask something they genuinely care about. Salespeople need to be authentic to connect with the person on the other end of the phone.
If they're not sharing what they actually care about in the interview, and instead ask something like "What do you think is Clari's biggest growth lever?" — forget it, no one actually cares about that in an interview.
Honestly, if you say, "Hey, I always ask interviewers one of my favorite questions: Harry, what's one thing about your company you'd most want to change?" Nine times out of ten, you'll catch someone off guard, and they'll share their real opinion, what they actually care about.
I think with intellectual curiosity, you have to know something about your product, your space, your customers, and be authentic about it — show up as your real self in the interview.
Harry Stebbings: If a candidate is purely money-motivated, is that challenging? If I show up and say, "Ben, look, I'm not the intellectually curious type, I don't really care about forecasting, I'm just a closing machine, I love the sales game, I can sell anything."
Ben Fiechtner: If they check every other box, I have no problem with that, if money is truly your number one driver. I think most salespeople try to hide that, but there's nothing wrong with it. As long as you're authentic about your reasons, it helps me understand two things:
First, how you fit into the company culture; second, how I can help keep you motivated.
Harry Stebbings: What's the best question a candidate has ever asked you?
Ben Fiechtner: My favorite, and one I ask almost every time I talk to someone, is: "Is there anything I should have asked you that I didn't?"
It's a closing summary question at the end of a conversation. It's like a soft close before the close. So it's a great question. I ask it almost every time at the end of a customer conversation, and I think the same applies for candidates in interviews.
Harry Stebbings: What skill has contributed most to your success, even if you're a bit guarded and reluctant to admit it?
Ben Fiechtner: There are two things I think about often.
Early in my career, it was definitely my fear of failure. I was very driven by this mindset — I couldn't accept failing at anything, I had to outwork everyone else, grind, do everything I could to make sure I didn't fail.
I was talking to our CEO about this the other day. If ten years ago when I was 30, you wanted to bike faster than me, I would have desperately tried to stop you. I had this competitive mentality about everything, even completely trivial things. I think that used to matter — a competitive-driven powerful motivation.
The second thing is, I don't want to let people down. I think this probably makes me a good or at least competent team leader, and it's also about the impact you want to have on customers. From that perspective, I want to make sure they walk away satisfied.
I'm a bit embarrassed to say this — I don't want to be someone who just tries to please people, or seems insecure, always worried about what others think of me. But a lot of times that's exactly what it is: I really don't want to let people down. I want them to have a great experience, whatever the conversation, interaction, or purchase.
Harry Stebbings: From everything we've discussed, I think your greatest strength is your authenticity, but your greatest weakness is also your authenticity and kindness. It lets you build very genuine relationships, but it also means you delay difficult decisions and struggle with making them. That authenticity and kindness is both a gift and a challenge.
Ben Fiechtner: I think that's fair and balanced feedback. Maybe the area I most need to improve is being more decisive as a sales leader.
I've learned now, Harry, that if I'm direct with you about what needs improvement, that's actually the most helpful thing I can do for you. It's more effective than trying to be diplomatic and worrying about letting you down. That's something I've worked hard to improve over the past three to four years.
Harry Stebbings: Do you do role-play in interviews? A lot of times, my own team and I aren't fully prepared, and it ends up being like, the person actually asks a good question, and we're trying to play an overly harsh CFO.
Ben Fiechtner: So I eliminated role-play. We moved to a different approach where the candidate has to prepare a customer plan, present an executive point of view.
We'd pick a customer within your territory. We'd say, "Come on, you're going to act like you're preparing an executive meeting for your boss and your boss's boss."
You need to help us understand what the executive point of view is, what their biggest challenges are, how we uniquely solve those problems, and how we'd prepare for the meeting. I think you learn a lot about how salespeople prepare from this.
It goes back to that original question — can they form a sharp, executive-level point of view that earns them the meeting and creates value for the customer.
Harry Stebbings: So, what's the most common way people screw up the interview?
Ben Fiechtner: I just don't think they're prepared. If you can't prepare for an interview, how are you going to prepare for a customer meeting?
Harry Stebbings: I might say, well, maybe they have ten interviews. They might actually perform differently on the job, but I completely agree with you.
Ben Fiechtner: Even if I'm not always interested in a particular role, I have to perform exceptionally well. So that even if I don't want that position at the time, they'll remember me in the future when they're thinking about me.
The same applies to HR. I come prepared with unique points of view. I think that's the minimum — the only thing you can control is your attitude and your preparation, and that's not hard to do.
Harry Stebbings: Alright, going back to our earlier thread — we have attitude, we have talent, what else?
Ben Fiechtner: Authenticity. I think we touched on this earlier. I've seen so many contrived salespeople who think this is what a salesperson should look and act like, and it rarely works.
When you're genuinely yourself, people connect with you more easily. I think people want to buy from someone like that.
Harry Stebbings: Last element — let's talk about compensation. What's your biggest learning in designing comp plans, and what makes them attractive to reps?
Ben Fiechtner: I think we've given this some thought. At Clari, for example, we have "hunters" (focused on new customer acquisition) and "farmers" (focused on existing customer expansion).
We also moved our enterprise team to a hybrid model, meaning they have both existing and new accounts. I think comp plans are often designed as an afterthought.
My only major learning is that you need to decide your GTM strategy. Of course, that'll require input from finance — margin targets, profit targets, growth targets, etc. — design your sales alignment and sales process, and then the comp plan should follow to reinforce those things.
We see all too often that comp plans are just minor tweaks to last year's plan, rather than a comprehensive review of overall go-to-market strategy, sales alignment, sales process, talent, and targets, with the comp plan built on top of that.
Harry Stebbings: You mentioned "hunters" and "farmers" — I'm curious, I had Dave Kellogg on as a guest before, I love him. He said you never want your farmers competing against someone else's hunters. How do you prevent that?
Ben Fiechtner: By the way, I love him too. He had a recent blog post, I forget what it was, with six points that I thought was the greatest career advice ever. It was incredible — I shared it with my entire leadership team.
On this question, how do you make sure your hunters aren't competing against your farmers or someone else's farmers. I think you have to be very, very smart about choosing your segments.
Going back to your earlier question about where to place capacity for maximum return. For us, it was moving upmarket to enterprise. We initially did very specific account allocations for our enterprise reps — each rep got 100 accounts in their territory. But we realized that allocation probably wouldn't drive the outcomes we wanted.
So we decided we absolutely had to precisely choose the accounts we must win, invest more resources in those accounts, perhaps even beyond normal headcount.
So if you know your ICP (Ideal Customer Profile), and you know the unique solution you can provide for that customer set, you'll put the right people in the right places.
09 Rapid Fire
Harry Stebbings: Let's do rapid fire. I ask a question, you give me your immediate thought.
Ben Fiechtner: This is the lightning round, I love it.
Harry Stebbings: What sales tactic is outdated?
Ben Fiechtner: "This discount expires at the end of the month or quarter." It's like what a used car salesman would say, and people roll their eyes at it every time.
Harry Stebbings: What about "we take our big customers to Taylor Swift, we do these big golf events"? Does that still work?
Ben Fiechtner: Neither of those are my thing, but Salesforce sponsors F1 events, and I'm all in on that. A lot of people had a great time last weekend.
Harry Stebbings: What's the most important lesson you learned from UiPath?
**Ben Fiechtner: Be incredibly smart and design your sales team around PMF.
When I joined UiPath, our business was geographically organized. I was fortunate to run their key accounts program, which was their top 100 accounts. I had banking and healthcare clients — JPMorgan Chase, HCA, world-class. We found an incredible opportunity, but we hadn't really planned for it. We were like peanut butter, spread everywhere.
We said, my God, healthcare and banking are our biggest installed base, but they're also our biggest opportunity. Because our technology was incredibly relevant to the problems they were facing at the time.
As a second-line leader at that point, I had already decided to go all-in and build support around me. It certainly wasn't just me, but like, my God, we found a unique PMF. Don't be afraid of verticals, don't shrink from it. We went bold, and it worked.
I've had many times in my career where I saw similar success, but I thought maybe it was an exception. That one, it was shockingly, this really works. We went all-in, the company rallied, and we made it happen.
Harry Stebbings: What's the biggest reason CROs and sales leaders disagree?
Ben Fiechtner: I think the problem is, oftentimes a CRO comes in with a ready-made playbook or experience — "I did this at this company" — and tries to apply it.
They should know the knowledge and frameworks, but more importantly, listen to what this company or sales team actually needs, and then design a playbook that fits them.
I think a lot of times when I talk to CROs, they'll say, "This is what I did at that company, why isn't it working here?" Every company has different challenges.
Everyone has their own unique piece on their growth journey, and you need to be very smart about solving the problems this company faces, rather than bringing the "tactical playbook" from your last company to the new one.
Harry Stebbings: If you could go back in time, what do you wish you knew when you first got into sales? Especially those early days at Salesforce.
Ben Fiechtner: That's interesting. I think I felt like I had to be someone I wasn't, because the Salesforce model was very uniform at the time.
There was an executive at Salesforce who pulled me aside and said just one thing: "Be yourself. Don't overthink it, don't try to copy this person's approach, don't become that personality. Just be yourself, be authentic." I think that was the biggest breakthrough in my career.
Not everyone is a big hitter, not everyone is incredibly social, not everyone is truly that data-driven, ROI-focused, detail-oriented salesperson. I think you play to your strengths rather than trying to be someone you're not.
Harry Stebbings: What's the secret to a happy marriage?
Ben Fiechtner: The most important thing I'll say about marriage is, be yourself and share how you actually feel. I think as I've gotten older, I've put as much time and energy into my marriage as I have into my career.
Harry Stebbings: What do you mean by putting more energy into your marriage?
Ben Fiechtner: Here's how I think about it. I've talked to so many CROs — if their CEO called right now, they'd immediately say, "Hold on, I need to take this." But if their wife called, how many would do the same? Very few, especially at certain senior levels.
So I think first, be honest with yourself about what your priorities are, and actually set some boundaries and rules to make sure you're prioritizing your spouse, your kids, your partner, or whoever else matters to you.
I think you have to put in the same effort. You have to show the same enthusiasm seeing your kids at 6 p.m. as you do showing up for a customer meeting at 8 a.m. That's probably a lesson I've learned in the last five years. It took me a long time to make sure I was putting as much energy into my personal life as my professional life.
Harry Stebbings: That's hard. Really hard.
Ben Fiechtner: It's interesting — I started my career at GE, and I remember we had a roundtable where everyone was asking questions. There were 12 of us in the room, and one person stopped and said, why aren't any of you asking me "how often do I see my kids?"
He was very frank — if you want to sit in my seat, accept that you'll be scheduling time with your kids on Outlook. I do take private jets, which is cool, but I'm on a plane 272 days a year. So you all want my job, but this is the reality of what comes with a seat like that. This was the early 2000s, late '90s.
I hope that with Zoom becoming ubiquitous, things have changed. And I think one of the great things about being in sales is that you have more control over your own schedule. I'm taking this call from home right now — I can spend 30 minutes with my kids between five and six, then come back. So you can have more flexibility in this era.
Harry Stebbings: Ben, I've loved this. Thank you so much for answering my weird questions, but you've been so good.
Ben Fiechtner: Harry, it's been my pleasure, and I've really enjoyed the opportunity to do this interview with you.
Translated by Stone
Edited by Wendi
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