Oct 23, 2024 · 1h 8m · news
AJ Tennant: How to Build a Sales Machine and Where Most Go Wrong | E2118 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this in-depth interview, host Harry Stebbings sits down with AJ Tennant, VP of Sales at Glean, to break down the mechanics of building a high-performing enterprise sales engine, navigating generative AI budgets, and scaling GTM teams.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 20.5% of the talking time here. How this is scored →
Harry as informed peer 2.8 Guest teaching 4.1 Guest disagreement 1.7 Harry pushing back 2.1
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 41:52 AJ rejecting Harry's premise about sales rep intelligence
AJ forcefully pushes back on Harry's assertion that sharp people avoid sales, asserting that tech sales attracts top-tier minds equivalent to banking or consulting.
Hardest push from Harry ▶ 21:01 Harry insisting on verticalized sales teamsHarry forcefully challenges AJ's generalist sales model, arguing passionately that win data from T-Mobile justifies creating dedicated telecom sales reps.
Biggest teaching moment ▶ 28:33 AJ reframing the customer success handoff modelAJ directly corrects Harry's framing of an account handoff from AE to CS, explaining that AEs must remain attached to drive upsell and deployment.
Harry holds his own ▶ 12:53 Harry detailing operational hurdles of enterprise upmarket expansionHarry demonstrates deep SaaS domain knowledge by pressing AJ on the heavy product, compliance, and legal overhead required when moving upmarket.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Are Sales Skills Born or Learned? | 2 | 3 | 1 | 1 | Harry asks whether sales skills are born or learned and follow-ups with observations on Mormons and young reps. AJ provides a detailed perspective on how sales can be learned and where reps struggle with flexibility. | |
| The Pitfall of Volume Over Depth in Outbound Sales | 3 | 4 | 3 | 2 | Harry questions the desire for volume over depth in outbound sales and asks about sales playbooks. AJ offers a slightly contrarian take on playbooks, arguing they overcomplicate simple sales fundamentals. | |
| The Role of Founders and CEOs in Early Sales Strategy | 2 | 4 | 1 | 1 | Harry asks whether founders should design early sales playbooks or delegate. AJ explains how founders like Stewart Butterfield and Arvind Jain stayed in the trenches early on before delegating strategy later. | |
| Understanding the Mid-Market: Contract Size and Sales Cycles | 3 | 4 | 1 | 2 | Harry drills into specific metrics like ACV and sales cycle duration in the mid-market segment. AJ breaks down the average 4-5 month cycles and shares key lessons on collaborative tension between R&D and sales from Slack. | |
| The Importance of Moving Upmarket Aggressively | 4 | 4 | 2 | 4 | Harry pushes back on the feasibility of moving fast upmarket due to product, legal, and compliance bottlenecks. AJ counters with how Glean strategically picked T-Mobile as a Fortune 100 anchor while segmenting sales teams. | |
| The Ultimate Challenge of Enterprise Sales: Security and Legal | 4 | 4 | 2 | 4 | Harry continues pressing on whether rapid upmarket expansion is realistic given the bloated overhead required for enterprise security and legal. AJ details how phased rollouts prevent early-stage companies from starving their reps of short-term revenue. | |
| The Art of the 'Land and Expand' Strategy | 3 | 4 | 1 | 1 | Harry asks how willing sales teams should be to accept small land contracts with enterprise clients. AJ emphasizes that land deals must be tied to explicit, time-bound success criteria to ensure conversion to seven-figure contracts. | |
| Resisting Early Vertical Specialization | 5 | 4 | 3 | 7 | Harry forcefully argues that having win data from T-Mobile justifies creating verticalized sales teams for telecom. AJ pushes back, arguing that staying generalist is crucial until hitting $200M+ scale to avoid operational complexity and geographic coverage issues. | |
| Why AI Budgets Are Still Experimental | 3 | 5 | 1 | 2 | Harry asks what makes current AI budgets 'experimental' and presses AJ to reveal Glean's largest contract size. AJ clarifies that budgets without defensible ROI will churn, while disclosing a deal size well north of $5M. | |
| The Implementation Gap in Enterprise AI | 3 | 5 | 2 | 2 | Harry asks why large enterprises struggle to implement AI tools and what buyers get wrong. AJ explains how enterprise AI sales suffer from a gap between pitch and implementation, citing Copilot falling flat due to change management issues. | |
| The AE-CS Partnership: Moving Beyond the Traditional Handoff | 3 | 5 | 2 | 2 | Harry asks how to seamlessly hand off closed accounts from AEs to CS reps. AJ rejects the 'handoff' framing, explaining that AEs at Glean stay attached to accounts to drive upsells while CS focuses on user activation metrics. | |
| Allocating Customer Success Based on Upsell Potential | 3 | 5 | 1 | 1 | Harry asks what contract thresholds justify dedicated CS support and probes SaaS retention metrics. AJ points out a common mistake: allocating CS based on initial deal size rather than total account TAM potential. | |
| Time to Launch and Active Usage as Leading Metrics | 3 | 4 | 1 | 1 | Harry questions whether upcoming AI renewal cycles will trigger mass churn. AJ confirms churn is already occurring for superficial AI add-ons and discusses optimal compensation structures for CSMs and BDRs. | |
| The Power of Aggressive Sales Comp Accelerators | 3 | 4 | 1 | 1 | Harry asks what AJ would modify in Glean's sales compensation plans and how he structures hiring interviews. AJ advocates for aggressive uncapped accelerators for top performers and explains the chronological 'Who' hiring method. | |
| The Strategic Prioritization Interview Challenge | 2 | 5 | 1 | 1 | Harry asks about panel interviews and candidate evaluation. AJ shares his specific interview tactic of forcing candidates to list and rank 10 data points on the fly to test creative problem-solving under pressure. | |
| Why Smart Minds Should Choose Tech Sales | 4 | 4 | 7 | 6 | Harry provocatively claims that top-tier intellectual talent avoids sales careers due to lack of IQ. AJ forcefully pushes back, arguing enterprise tech sales offers complex problem-solving equivalent to banking or consulting and attracts brilliant minds. | |
| Are Sales Reps Coin Operators? | 3 | 4 | 2 | 3 | Harry asks if sales reps are purely coin-operated and questions the validity of panel interviews. AJ refutes both points, framing panel interviews as vital simulations of real multi-stakeholder buyer presentations. | |
| Designing Effective Executive Interviews | 2 | 5 | 1 | 1 | Harry asks how quickly bad sales hires become apparent and what mistakes occurred during AJ's own hiring at Glean. AJ explains that underperformance is visible within 30-90 days and defines 'collaborative tension' as a core requirement for success. | |
| Leadership Mistakes, Speed, and the Power of Enablement | 2 | 5 | 1 | 1 | Harry asks about AJ's historical leadership mistakes and common onboarding failures. AJ admits to moving too fast when filling roles at Slack and reflects on how he shifted from dismissive of enablement to seeing it as critical. | |
| Quick Fire: Discounting Matrix and Logo Credibility | 2 | 4 | 1 | 1 | Harry runs a quick-fire round covering discounting, logo social proof, and creative deal-making. AJ shares a story about stalking T-Mobile CEO John Legere at a hotel bar to build rapport before an enterprise pitch. | |
| Goals, Performance, and the CEO Path | 3 | 4 | 2 | 2 | Harry asks about maintaining team morale during missed quarters and probes the CRO-to-CEO career path. AJ outlines how sales leadership prepares executives for the CEO role and praises Wiz's partner/channel distribution strategy. | |
| Harry Stebbings on the Skepticism and Grind of Venture Capital | 0 | 1 | 0 | 0 | AJ turns the interview around, asking Harry about the hardest aspects of his career. Harry reflects on facing constant skepticism from incumbents and describes the decade-long relentless grind required to build 20VC. |
Statements from this episode (76)
AJ Tennant: Underperforming AEs bring problems without solutions
“You can very quickly know when you've got an AE that's all they're doing is coming to you with problems and not coming with solutions and ideas.”
AJ Tennant: Steamrolling team members instead of collaborating will get reps fired
“If you do not have the ability to collaborate effectively in a way that's driving your point of view that does require some tension and you are steamrolling people, people don't want to work with you, you're gone.”
AJ Tennant: Sales skills are entirely learnable, not innate personality traits
“I fundamentally believe they can be learned. You know, I think a lot of people would say it's innate, you know, you, you're born with it, it's that your personality, someone that's outgoing, but my philosophy is that pretty much humans can learn anything if th…”
AJ Tennant: Junior sales reps fail by relying on rigid pitch scripts
“I would say AEs are really struggling as being super creative and flexible and nuanced when you're engaging in a live conversation with someone. So, everyone has an idea when they're going into a call of what to say. They first think they're gonna get rejected…”
Tennant: Best Account Executives Do Their Own Outbound Prospecting
“Absolutely. We at Glean, you know, we have a, you know, and every company I've been a part of, like, I want AEs to be joining, expecting that they have to do outbound, and they're not going to have a BDR. Now, the reality is, is you're going to have a lot of h…”
AJ Tennant: Sales playbooks overcomplicate sales, which is fundamentally simple execution
“My view is that playbooks are really, it's like a fancy word for what is your strategy? What is your outbound messaging? Like, what is your plan? Like a play, so I guess, you know, it can be semantics a little bit, but what I view is sales is very simple. You …”
Founders must lead sales directly from zero to $10M ARR
“I think that the founders need to be very involved, and the CEO needs to be very involved in that, that zero to ten million On, on kind of like how you're getting those initial customers to product market fit”
AJ Tennant: Stewart Butterfield and Arvind Jain personally drove early sales
“At Slack, Stuart was very involved on figuring out how to get those first customers and making them successful. Arvin, the same thing at Glean”
AJ Tennant: Mature founders shouldn't dictate granular sales plays or messaging
“There's a stage at which you need to have that founder and CEO not necessarily, like, be deciding exactly what is the messaging, exactly what is the sales play that you're running, and they need to, you need to leverage them, but they shouldn't be the one dete…”
Selling to Fortune 100 and SMBs simultaneously will kill early startups
“If you all of a sudden are trying to go to the fortune 100, and also sell to SMBs, you're gonna fail.”
Tennant: Middle market is ideal for early SaaS startups seeking product-market fit
“I think, like, for technology, SaaS products, a really good place to sell to is in that middle market space, and going after that, and getting to product market fit, you get more cycles, more at-bats.”
AJ Tennant: Glean's mid-market annual contract values are well over $100,000
“Yeah, a little, little north of that, like you could get you know, in that, that segment right now, we're well north of that, but when we were getting going early, early days, where even before I was there, that's even, that's what it would be.”
AJ Tennant: Glean achieves 90-day sales cycles for sub-1,000 employee accounts
“It is, but I, on the sub-one thousand, we're getting it down to, you know, 90, 90 days. So it's closer to the four if you blend in that, like that below a thousand.”
Tennant: Tech startups must build collaborative tension between R&D and GTM
“The number one takeaway that I, I've brought to Glean. It's what I give to other, you know, founders I advise and just is how important it is to have the collaboration and like collaborative tension between R&D and GTM.”
Tennant: Bring R&D and product leaders onto customer sales calls
“I mean, that, and I, my lesson was bringing those individuals onto the calls. Get R&D onto the calls to hear the feedback. We needed to get engineers and R&D and Product leadership to hear and have empathy for the customer.”
Horizontal products with PMF should move upmarket faster and more aggressively
“It is important when you have, like, such a horizontal product like Slack that has product market fit to move upmarket faster and more aggressively.”
Slack segmented sales into SMB and enterprise at $10M ARR
“When I joined Slack, I immediately, after we got to about ten million in revenue, Cut the team into SMB and enterprise, and I basically said enterprise is a thousand employees and above, SMB is below, and that way we just sort of put the resourcing, the more e…”
AJ Tennant: Glean defined enterprise sales as 2,000-plus employee companies
“At Glean, when I joined, we had real great success in that mid-market segment. We had strong sellers, about like eight of them, and we decided very quickly with the team to say, we've got to move up market, let's cut it at 2000 employees and above, and the bel…”
AJ Tennant: Winning T-Mobile ignited Glean's upmarket growth momentum
“T-Mobile became that account for us at Glean. Not just a sales team, as a company and leadership team, we said, we are going to prove success at a Fortune 100, Like T-Mobile, get it to, get a win, get value, get success, and that's what we did. And then, as so…”
Tennant: R&D teams underestimate enterprise security and legal friction
“I think people underestimate, especially R&D organizations, like, how you're gonna navigate security, deployment, POCs, pilots, like, all of that nuance of getting through that, not to mention legal and contracting, becomes just, it's like molasses.”
Glean co-founder spent 20 hours on security calls for single deal
“I remember having conversations with Vish, one of the co-founders of Clean, he's like, AJ, I've been on 20 hours of calls with, you know, with this account for the same conversation about security issues.”
Glean phased its upmarket transition by giving reps key accounts alongside mid-market
“What we did was we said, okay, this team that's going after the, 2003 1004 1005 thousand, maybe even we started selling to like 10,015 thousand person accounts. We said, we're going to give you one or two of these key accounts that we're going to try to get in…”
Early-stage sales teams should not segment or rush upmarket too early
“I think the worst thing you can do early stage as a sales organization and a go to company is segment too early and move way up market and just like, let's say we rewind the clock. If I all of a sudden moved all my sellers to just focus on the Fortune 50 or Fo…”
Tennant: Enterprise land-and-expand deals require upfront executive alignment on expansion metrics
“I think you need to be very willing to do that. Now, the key thing that we've learned, and I, you know, learned this at Slack as well, but at Glean, You've got to have success criteria. You've got to have, okay, we're going to do, let's say for Fortune, 100 co…”
Tennant: Glean converted a Fortune 100 pilot into a seven-figure contract
“We had one Fortune 100 companies say, we want to test how you're, how we're lowering call resolution time with Glean relative to the other solution we had and the competitors. It was very time bound. It was very specific. And we're able to tie that back exactl…”
No enterprise has fully figured out its AI strategy yet
“Absolutely. I think, like, no, any company that's gonna say, oh, we figured out what we're doing with AI, I don't think they're, I don't think they figured it out.”
Glean Sales Strategy: Grounding raw AI demand in defined business value
“Our strategy is to capture that AI demand, but then turn it back into clear business value that has success criteria.”
Sales teams should remain generalists until hitting $200M to $250M revenue
“I hear that argument. I still think staying generalist is important until you get to a certain scale. I think you need to be at 200,000,250 million to go that granular because Just the number of AEs that you need to hire to get to vertical, just become, and it…”
Tennant: Regional Generalist AEs Beat Sector Specialists for Global Accounts
“I think that you can solve that by educating Some of the other generalists AEs because the problem with it is sometimes, you know, those telecoms are all over the world, right? And you're not going to have one AE who's based in the, you know, the Bay Area be a…”
Enterprise AI spending remains experimental due to lack of defensible ROI
“I call it experimental because people are still not defining it all the way back to a business issue and an ROI that is, like, fully defensible.”
Enterprise AI tools without clear ROI will churn within two years
“AI budgets that are based on just, hey, we need to quickly enable our employees to be AI-centric that aren't tying it back to business outcomes, impact, Top line, bottom line. A year from now, two years from now, we're going to churn.”
Tennant: Enterprises spend $5M-$10M annually on non-experimental AI initiatives
“Like, you've got a couple of these big, big brands and companies that are doing AI in the right way that's actually impacting their top line or bottom line already that isn't experimental, right, and they're willing to spend, some of those accounts are willing…”
AJ Tennant: Glean's largest customer contract is well north of $5 million
“You know, well, well north of five million.”
Enterprise AI implementation takes 6-12 months or $5M in services
“Everyone is being sold A bag of goods and a dream of this sort of AI enabled workforce or Automation, top line, bottom line, and then when it comes to implementation, it's taking six, nine, 12 months, or it comes attached with a five million dollar services bu…”
Many enterprise customers say Microsoft Copilot is falling flat
“Look at like Microsoft Copilot, I mean, Many customers are saying it's falling flat. Like, it's just not delivering the value that was advertised.”
Tennant: Enterprise AI friction stems from security and change management, not product
“So what the challenge is, is not like some of the other technologies, a product issue, it's more of a change management security challenge.”
Glean withholds AE commissions unless deployment success plans are completed
“I took a page out of Dave Schneider's book from ServiceNow and We're implementing a system where we're not paying AEs on their deals unless they have an approved deployment success plan filled out.”
Tennant: Tech companies fail by postponing deployment planning until post-sale
“It's a lot of companies are Getting the big deals done, and then assuming, okay, we can figure out the deployments later, and that's what they get wrong.”
Glean requires enterprise Account Executives to stay involved during deployment
“Our strategy is that in the enterprise, you as an AE are involved in the deployment. The reason you're involved is because you have an incentive to make them successful because your, the future upsell is dependent on your ability to drive deployment.”
Glean ties CSM compensation to user activity rather than direct upsells
“We're actually tying the compensation of our CSMs not to an upsell. I guess it's sort of embedded into the NDR piece, but it's frankly more about, are you getting users active?”
Glean expanded a $60K healthcare deal to over $500K in 9 months
“We had this healthcare company do a 60,000 dollar land deal with us, and over the course of nine months, the AE, the SE, and the CSM turned that account into a 500,000 dollar plus contract because they focused on deployment, they focused on success, they tied …”
AJ Tennant: Slack assigned senior CSMs strictly based on account ARR
“So I think one thing that I learned at Slack is like all Slack did was look at What the ARR was for the specific account, and then tied it, and they would only put a senior CSM on the, you know, whatever, the million dollar contracts.”
AJ Tennant: Junior CSMs on enterprise accounts reduce upsell likelihood
“If you are closing, let's say you close a couple hundred K deal with Exxon Mobil, and you're putting like a junior CSM on it who doesn't know how to navigate, you're gonna have, you're not gonna be likely to drive an upsell.”
AJ Tennant: Gross retention rate is the most critical enterprise SaaS metric
“Most important for me is GRR. Why? Churn. Like, the ripple effects of having an account in, especially in the enterprise space, churn, it, it's the viral negative network effect that happens.”
AJ Tennant: Glean maintains a 97% to 98% gross retention rate
“And so, you know, luckily at Glean, we have like a 97, 98% GRR. The only accounts we're churning are SMBs,”
AJ Tennant: Fast product launch and active usage make SaaS retention trivial
“Because if you nail in a systematic way time to launch quickly and you get active users, GRR is just an afterthought. It's going to be, it's not going to be a problem, right? If you have people using the service and they're using, getting deployed quickly.”
Vertical software AI add-ons will suffer high churn
“I also, I think that you're gonna see it, for example, like, there's some of these vertical solutions that have layered on to AI and sold a big story on, hey, you're already you know, paying X with us. We can accelerate you to go faster. I don't think some of …”
Tennant: Comping BDRs on closed-won deals takes too long
“Comp BDRs on not net new opportunities, but comp them on closed one. I think it's too far and too long of a thing to do”
Glean gives spot bonuses to CSMs for multi-million dollar expansions
“Actually, we did that at Glean, but we haven't systematically done it. So, for example, you know, the companies that did these multi-million dollar expansions, we actually strategically gave a large spot bonus to the CSM that was on that because we wanted to r…”
Aggressive accelerators are the single best sales compensation lever
“More aggressive accelerators. You know, accelerators are essentially ways to, if someone goes over a hundred percent of their quota, An accelerator just gives that rep the ability to move faster in terms of accelerated comp. And so what it's doing, and why I s…”
Stebbings: Early-stage founders make their biggest mistakes in hiring
“Hiring is really freaking hard. Like it is the one area where I think most early stage founders get most wrong.”
Tennant: Chronological interviews reveal a candidate's true underlying motivations
“Understand the deep history of the individual Over a chronological period of time. I didn't realize that that was a hiring methodology until Bob Fratty taught me that at Slack, which is kind of this who hiring, the who hiring method is what we call a chronolog…”
Bypass polished sales pitches by asking for specific manager references
“One approach to this, which is in the Who hiring method, is you ask people while you're going through that process of, who is your boss? Who is the hardest person you worked for? Who is someone, like, you didn't like working for? And then you, in the moment, s…”
Tennant: Sales interviews must test quick strategic thinking over canned answers
“What I'm looking for in that question is actually like higher level thinking of like, how can you think not only quickly, but strategically and then map it to what is actually going to be your job? Like you are going to get a hundred accounts and you are going…”
Harry Stebbings: Sales reps failing at strategic thinking lack general intelligence
“I think it's IQ. I think people are just not that smart.”
Harry Stebbings: Truly sharp people avoid tech sales account executive roles
“If you, if you're a really sharp, insightful person, you're not going to be an AE. I'm going to get killed by a whole AE audience. But like, if you're really sharp, I can make money in so many better industries. It's tough. Sales is fucking hard.”
Tennant: Product and sales drive tech, non-engineers should pick sales
“In technology companies, and this might be controversial because like, you know, this is like putting aside like all the other things that make these companies go. There is product. And then there is sales. Like, what drives technology companies and most busin…”
AJ Tennant: Coin-Operated Sales Reps Are the Ones You Shouldn't Hire
“The sales reps that are coin operated are the ones you don't want to hire. The sales reps that have that insightful IQ that you talked about want career development. They want challenges. They want to figure out how to get, like, coached and mentored. That's w…”
AJ Tennant: Panel interviews are essential for testing sales candidate IQ and EQ
“I think that a hiring panel is equivalent to You showing up to a customer meeting, and there's three or four people that are in the room that you are presenting to. A hiring, like a panel presentation is, for me, an opportunity to see how someone is going to h…”
AJ Tennant: Slack required all AE candidates to complete a writing exercise
“At Slack, anyone that was coming in as an AE had to do a writing exercise, and it wasn't a take home, like I think you just had to write something.”
Tennant: CEOs Should Have Executive Candidates Solve Active Company Problems
“I think that having him ask me, hey, AJ, here are the three problems that we're dealing with as a company right now. Can you produce something and present to me and my leadership team on how you're going to solve it? It has two benefits. Even if I don't turn o…”
Glean Tests Sales Candidates on Active Prospective Target Accounts
“One of the strategies we have in our panel interview is, I always ask my managers, it's a double, like, choose the account that this person is prepping for their sell to, On a new prospect that we are trying to get into.”
Tennant: Enterprise sales underperformers are identifiable within 60 to 90 days
“So if we're talking about the enterprise segment, you're gonna know within six, probably 90 days.”
Tennant: SMB sales underperformers are identifiable within 30 to 45 days
“SMB you're gonna know in like 30, 45 days.”
Tennant: Glean maintains an all-time sales turnover rate of around 20%
“We have about, ah, all time, like a 20% turnover rate.”
Tennant: Ability to manage collaborative tension is essential in hyper-growth startups
“If you can't do that effectively, then you need, you can't be a part of these hyper-growth companies, because that's what they need to make progress.”
AJ Tennant: Skipping sales enablement hurts startup performance in the long run
“Founders and sales leaders that have the mentality that I have like had back then who are just like, let's hire the best reps. They can figure it out. It, it's gonna hurt you in the long run”
AJ Tennant: Startups past $10M-$20M ARR need a strict discounting matrix
“I approach it early days, do it, get the deals done, but once you get past, like, 1015, twenty million in revenue, you really need to have a very tight discount matrix, and don't give away just horrible deals, because it's gonna impact the market discount rate…”
AJ Tennant: Customer success drives subsequent sales better than brand logos
“If you get a marquee customer and get them successful, it's more important than the logo, it's actually, they will do reference calls, they will do intros, so I think it's less about the logo, and it's more about that customer becoming successful to then do re…”
AJ Tennant met T-Mobile's CEO at a bar to impress the CIO
“I knew the CEO at the time, John Ledger, used to hang out at the W Bar in Seattle, and so, Before an on-site, that night before, I just stayed in that W bar, like, just hanging out, and John Ledger came in, and I went up to him, and we spent time chatting. And…”
Tennant: Effective standard goals are beatable while stretch goals target 80% completion
“No. Effective goals are goals that you can achieve and you can outperform. I think that effective stretch goals Are ones that you can only get to 80%.”
AJ Tennant: Wiz built a phenomenal channel distribution strategy
“What they'done with their partner and channel strategy is just phenomenal. You know, they have a direct sales motion, but what they did is they went to the sort of channel, whether it was the hyperscalers and the cloud service providers, but more importantly, …”
Slack lost to Microsoft by over-relying on product-led growth
“We lost the distribution war at Slack. I think part of why we lost that war was, yes, like, monopolistic behavior by Microsoft, but Because we didn't lean into other effective fast distribution strategies other than PLG.”
Harry Stebbings has not taken a weekend or holiday in ten years
“And like, I haven't had a weekend in 10 years since I started. I haven't been on holidays for 10 years.”
Shorts cut from this episode
▶ Do smart people still work in sales? 🧠 · 20VC with Harry St (@43:48)
▶ My biggest lesson from Slack 🧠 · 20VC with Harry Stebbings (@9:52)
▶ 2 reasons sales reps fail ❌ · 20VC with Harry Stebbings (@0:00)
▶ Are hiring panels worth it? 💼 · 20VC with Harry Stebbings (@46:42)
▶ The best way to win a deal? 🤝 · 20VC with Harry Stebbings (@59:43)