Steven Regimbal

Enterprise Sales | Partnerships | GTM
Scaling SaaS companies from $1M → $10M ARR.
Reggie’s Playbook

[Steven Regimbal @StevenRegimbal]

@Kazanjy What tells you the win rate will transfer from the founder to the first AE? I’d be curious how you separate a repeatable sales motion from deals that still depend on the founder’s credibility or product knowledge.

[Steven Regimbal @StevenRegimbal]

@jjen_abel How would you test for that in an interview? I’d be more interested in how a candidate unpacks a messy deal—what they noticed, what they missed, and how they changed the approach—than in a polished pitch.

[Steven Regimbal @StevenRegimbal]

@alexdanilowicz Is the friction budget approval, or the change the customer has to make? A $10k tool can still touch a sensitive workflow. I’d want to separate those before deciding whether the fix is a simpler buying path or stronger sponsorship.

[Steven Regimbal @StevenRegimbal]

@spenserskates As usage moves into agents, are you seeing a different person champion Amplitude inside the customer? I’m curious whether the buying conversation is changing too, or whether the same buyer is simply getting value through a different workflow.

[Steven Regimbal @StevenRegimbal]

@lennysan The ongoing mentorship could be the most valuable part. I’d have founders join a new seller’s first customer calls, then compare notes: what mattered to the buyer, what stayed unclear, and what to try next. Both get better, and the sales motion improves with them.

[Steven Regimbal @StevenRegimbal]

@jasonlk I’d add a second round to that test: give the candidate feedback after a short discovery exercise and let them try again. The first attempt shows how they sell today. The second shows whether they can learn alongside a product and sales motion that are still changing.

[Steven Regimbal @StevenRegimbal]

@alexdanilowicz The useful test is what happens when the rep has to choose between a fast close and a customer likely to expand. If the plan rewards only the signature, it can work against the product-led growth you’re trying to build.

[Steven Regimbal @StevenRegimbal]

@benhylak As you moved from startups to Fortune 100s, what changed most in the buying conversation: proving the agent works, or agreeing who owns the risk when it doesn’t? That seems like a useful distinction for founders building their first enterprise sales motion.

[Steven Regimbal @StevenRegimbal]

@jjen_abel The technical evaluation still needs to happen. I’d agree with the executive upfront on what it needs to prove and when we’ll regroup. That gives the product team a clear brief without losing the business sponsor along the way.

[Steven Regimbal @StevenRegimbal]

@FactoryAI Curious whether this changes who brings Factory into the account. Does an existing Anthropic commitment help an engineering champion move a pilot forward, or does it mostly simplify purchasing once the technical evaluation is complete?

[Steven Regimbal @StevenRegimbal]

@lennysan Before running one of these, I’d choose the buyer behaviour it should change and the next step to measure. A campaign that gets shared widely and one that creates qualified conversations can look identical in a reach report.

[Steven Regimbal @StevenRegimbal]

@jjen_abel I’d ask each seller to unpack one won deal and one that stalled: buyer role, deal size, what changed the next step, and what they misread. That context would help founders judge which tactics transfer to their own sales motion.

[Steven Regimbal @StevenRegimbal]

@shensi New-hire onboarding feels like a useful test for this: can someone produce work that meets the team's standards without a colleague rebuilding the brief? How do teams decide which lessons become shared knowledge, and retire guidance that has gone stale?

[Steven Regimbal @StevenRegimbal]

@Kazanjy A short ‘cost of doing nothing’ section could make this even easier to use. It gives the champion a way to explain why the change deserves budget now, alongside the ROI and implementation plan.

[Steven Regimbal @StevenRegimbal]

AI shouldn’t just make your company more efficient. It should make your people more effective. Don’t use AI to squeeze out 20% more work—give people 20% of their time back for customers, creativity, strategy and high-impact work.

[Steven Regimbal @StevenRegimbal]

Biggest deal you've ever closed?

What mattered most:

Product?
Price?
Timing?
Relationship?

My experience: TRUST.

[Steven Regimbal @StevenRegimbal]

Enterprise deals close on trust.

Features simply support the decision.

[Steven Regimbal @StevenRegimbal]

Enterprise deals don't close because of features.

They close because of trust.

The larger the deal, the more trust matters.

[Steven Regimbal @StevenRegimbal]

The best product alone doesn’t win.

The best-distributed product does.

That’s why I’m obsessed with GTM, positioning, sales, and helping builders win.

[Steven Regimbal @StevenRegimbal]

Want to scale your sales team?

Start with this:

1. ICP definition
2. Messaging
3. Discovery questions
4. Objections
5. Closing

No playbook = no performance