Scaling Sales with Structure and Discipline with Tom Levey

With Tom Levey, Former Chief GTM Officer at DataRobot, Sales Strategy Leader at AppDynamics, Angel investor, and founder of a stealth startup funded by Sierra Ventures

Tom Levey has led go-to-market functions from seed-stage startups to pre-IPO giants. He helped build AppDynamics into a category leader and later scaled complex enterprise sales at DataRobot. His approach is grounded in operational rigor, not hype, hero sellers, or top-of-funnel hacks.

At Sierra,  we gathered our founders and sales leaders for an incredible session on scaling sales, led by Tom. This is a high-level overview of what Tom shared with the portfolio regarding structure, consistency, and people development to create GTM systems that scale.

Build a Sales Org with Discipline, Not Just Demos

Tom didn’t scale sales by relying on a category-defining product. He did it with process and discipline. The team’s six-month rep ramp wasn’t measured by time in seat or demo readiness. It was measured by whether a rep could source and close two “real deals” above $100K ACV. That benchmark defined everything: onboarding, coaching, and how they hired future leaders.

“The best product in the market does not always win. But the most operationally disciplined always wins; and that is what I help create.”

Key takeaways on what Tom did:

• Ramped = time to source and close two full-cycle deals (not shadow, not assist)

• Created a central playbook to encode high-performer behaviors into reusable assets

• Built a lightweight operating system to track ramp, stage progression, and rep-level signals in real time

• Benchmarked top reps with a program called the “Golden 7” to reverse-engineer every success measurement

• Continuously fine-tuned the onboarding flow based on what predicted future rep success

• This led to 50% reduction in rep ramp time and 78% of first-line managers promoted internally from within

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Flip the Funnel: Recruit → Retain → Revenue

Most sales leaders over-index on late-stage pipeline and short-term deals. Tom’s approach starts earlier, with hiring. If you recruit people with the right traits and give them a path to grow, revenue will follow.

“Revenue doesn’t start with pipeline. It starts with the person you just hired.”

Recruit:

• Hire for intelligence, character, coachability, and experience

• Never over-index and hire for experience alone. “Something about a candidate's past is typically a reason not to hire someone.”

• Begin every interview by selling the company, the culture, the product, and the opportunity, not interrogating the candidate. Once a candidate is informed and excited about the opportunity, you can proceed with the “tougher questions.”

• Never hire off the LinkedIn profile. It’s static and formulaic. Ask for the handwritten resume. “I want to see how someone chooses to tell their story.”

Retain:

• Know what your reps care about: their goals, families, and long-term aspirations.

• Rigorous and ongoing training focus.

• Formal training & development should be world-class. Create a culture where reps truly believe, “This place makes me better.”

Revenue:

• Drive predictable performance through repeatable execution:

• 10+ new business meetings per quarter

• 65%+ conversion to qualified opportunity

• 2+ forecastable deals per quarter over a “significant value” threshold

• Focus less on pipeline multiples and more on stage-by-stage discipline

Set the Standard Early: Onboarding as Culture

When most teams are onboard, they teach the product. When Tom onboards, he teaches how to operate with excellence. He believes onboarding is the foundation for culture. If you don’t set a high bar from the beginning, everything else falls apart.

“If you don’t set the standard, your reps will invent one.”

Key takeaways:

• Train reps on your company’s sales standards, not just messaging

• Codify excellence: what a great discovery call, email, quote, or POV looks like. Embedded feedback loops to continuously improve based on actual rep performance data

• Choose only one area per quarter (e.g. champion building or pipeline generation) and raise the floor across the team to achieve excellence.

• As the team grows, new reps will absorb the culture from those around them

Promote From Within, But Only with a Plan

Tom has promoted 100’s of salespeople into leadership roles, and 78% of them have come internally from within an organization. But he didn’t promote top performers overnight. He started preparing them six months before the role opened and made sure they knew how to lead different kinds of reps, not just clones of themselves.

“If you promote someone without preparing them, you’re not giving them a promotion. You’re handing them a 6x quota.”

Key takeaways:

• Don’t promote reactively. Develop future leaders early

• Teach ICs how to manage different styles of reps, not just mimic their own style

• Set expectations clearly: you’re building leaders, not super reps

• Leaders who come up internally are often better coaches. They’ve done the job

Use Business Value Assessments (BVAs) to Create Urgency

Many early-stage companies struggle with post-POC drop-off. The demo lands, the tech wins, and then nothing. Tom sees this again and again. He solves it with the BVA: a structured, customer-informed business case that creates urgency and makes it easy to say yes.

“If you’ve got technical sign-off but no budget, you don’t have a sales problem. You have a missing business case.”

Key takeaways:

• Always secure executive sponsorship before starting a BVA

• Interview 10 to 20 internal stakeholders to quantify pain in their language

• Build a model that says, “Here’s the value you said this solves, and here’s the ROI”

• Position it like $30K worth of consulting, delivered for free

• Deals with BVAs are larger, faster, and more likely to renew and expand

Simple, Not Easy

Tom’s approach is grounded in simplicity. Hire great people. Train them with discipline. Build a data-driven, evidence-based system where success is teachable and replicable. And reinforce it every day.

“Sales isn’t complicated. You stand at the edge of the pool, you jump in, and you swim to the other side. The hard part is doing that every day.”

Founders building their first sales team (or fifth)  should start here: clarity, consistency, and care for the people they bring on board. Everything else, from pipeline to promotion, follows.