The Twenty Minute VC

AJ Tennant: How to Build a Sales Machine and Where Most Go Wrong | E2118

AJ Tennant is the Vice President of Sales & Success at Glean, Glean has more than 20x'd its revenue and 100x'd its user base in the just two and a half years he's been there. Before Glean, AJ had incredible runs at Slack and Facebook. At Slack, AJ helped grow revenue from $6 million to more than $1 billion. ----------------------------------------------- Timestamps: (00:00) Intro (01:45) The Hardest Sales Skill To Learn (02:48) What Do Young Reps Struggle to Learn Today? (04:51) The Sales Playbook (07:22) Sales Team Structure (09:22) Takeaways From Working at Slack (12:08) Moving Upmarket (17:50) Small Contracts for Big Customers (22:01) Buzzwords (23:19) How to Sell AI Tools in 2024 (30:14) When Does It Make Sense to Scale Up CS? (34:02) Should CSMs Be Compensated for Upsells? (35:24) What Would You Change About Glean’s Sales Comp Plan? (36:01) Hiring Sales Team (40:05) Are Sales Reps Truly "Coin Operated"? (50:18) How To Improve Glean’s Interview Process (54:32) Hiring Mistakes (57:52) Quick-Fire Round ----------------------------------------------- In Today’s Episode with AJ Tennant We Discuss: 1. How to Sell AI Tools in 2024: Are we still in the experimental budget phase for AI? How does selling AI tools differ to selling traditional SaaS? What are enterprises biggest concerns when it comes to adopting AI tools? What buzzwords get enterprises most excited in the sales process? Will we see a massive churn problem when the first renewal cycle for many of these AI products comes? 2. Outbound, Discounting, Closing: Is outbound dead in 2024? What does no one do that everyone should do? How does AJ approach discounting? Biggest lessons and advice? What can sales teams do to create a sense of urgency in a sales cycle? How does AJ do deal reviews and post-mortems? What is the difference between good and bad post-mortems? 3. How to Master Customer Success: What are the biggest mistakes founders make today in managing their CS teams? Should CS be compensated for upsell? How should the comp structure of CS teams change? What can be done to create a good handoff experience for the customer when handing from AE to CS? What are the most common ways CS teams break over time? 4. Hiring the Best Sales Teams: How does AJ structure the hiring process for all new sales hires? What questions does AJ always need to ask when hiring sales reps? What are clear signs of outperformers when hiring new reps? Does AJ give candidates a take-home assignment? What does he want to see from them? How quickly do you know when you have made a bad sales hire? What are the signs of a bad sales hire? What goes wrong first? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow AJ Tennant on Twitter: https://twitter.com/ajtennant Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #ajtennant #glean #sales #hiring #customersuccess #slack #tmobile

AJ TennantguestHarry Stebbingshost

Oct 22, 20241h 8mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

AJ Tennant Reveals How To Build Scalable, High-IQ Enterprise Sales Teams

AJ Tennant, CRO at Glean and former early sales leader at Slack and Facebook, explains how to build a modern enterprise sales machine, especially for horizontal SaaS and AI products. He argues that sales is a learnable craft centered on creative problem-solving, resilience to rejection, and deep collaboration with product and engineering. The conversation covers moving from mid-market to enterprise, making AI pilots real business value, structuring CS and comp for expansion, and running a rigorous, IQ-testing hiring process. Tennant also emphasizes ‘collaborative tension’ across teams, the critical role of enablement, and why smart graduates should seriously consider tech sales as a primary career path.

IDEAS WORTH REMEMBERING

5 ideas

Sales is learnable, but demands resilience and creative problem-solving.

Tennant insists strong sellers aren’t just gregarious; they actively listen, adapt in real time, handle rejection, and come to leaders with solutions rather than problems.

Start in mid-market, then move aggressively upmarket once success is repeatable.

For horizontal SaaS, he recommends 500–4,000 employee accounts and ~100k+ ACVs to build product-market fit and cycles; once you’ve repeatedly won and delivered value for 5k–15k employee customers, segment your team and commit to enterprise.

AI deals must move from ‘experimental budget’ to concrete business outcomes.

Enterprises are eager and will spend millions on AI, but pilots churn if they’re not tied to specific, measurable success criteria (e.g., lower call resolution time) and clear ROI; vendors must help define those metrics.

Implementation and change management are now the real bottlenecks in AI.

Many AI projects fail not because of core technology, but because deployments take 6–12 months, require heavy services, and lack a deployment success plan; Tennant even withholds AE commission until such a plan is in place.

CS and sales should jointly own expansion, with CS measured on usage and retention.

At Glean, AEs stay involved post-sale and own upsell, while CSMs are comped on GRR/NRR and active usage, not just revenue; a $60k land grew to $500k+ in nine months by obsessing over deployment and value realization.

WORDS WORTH SAVING

5 quotes

Sales is very simple: get net new meetings, turn them into opportunities, and work them through a funnel.

— AJ Tennant

The sales reps that are coin operated are the ones you don’t want to hire.

— AJ Tennant

Everyone is being sold a dream of an AI-enabled workforce, and then implementation takes six, nine, twelve months.

— AJ Tennant

If you do not have the ability to collaborate effectively in a way that does require some tension, and you are steamrolling people, people don’t want to work with you—you’re gone.

— AJ Tennant

This is a game of who survives the longest.

— Harry Stebbings

Sales skills as learned behaviors vs. innate talentMid-market focus and timing/strategy for moving upmarket to enterpriseSelling and implementing AI tools in an ‘experimental budget’ environmentSales org design: segmentation, CS structure, comp plans, and enablementDesigning and running high-bar hiring processes for AEs and GTM rolesLand-and-expand strategy, deployment success, and churn preventionCollaboration and tension between Product/R&D and GTM in scaling companies

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