In this new episode of Path to Market, our Director Natasha Lytton and co-host Micah Smurthwaite, Partner at Pipeline Ventures, sit down with Tim Bertrand — a three-time GTM leader who’s scaled companies from just a few million to hundreds of millions in revenue. Currently serving as President of HAProxy, Tim previously held sales leadership roles at Acquia and Project44, and brings deep insights into category creation, founder-led sales, sales hiring, and international expansion.
Tim walks us through his career of building sales engines from the ground up — including Acquia’s leap from $2M to $200M+ ARR — and explains why he keeps coming back to the early-stage trenches.
He also shares actionable advice for founders: when to hire (and who to hire) in your first sales roles, how to think about pricing in new markets, how to align product and GTM, and what great onboarding and sales coaching look like.
Here’s what’s covered:
05:00 Early-Stage Sales: Why Tim Keeps Coming Back
07:12 Structuring Your First Sales Hires
09:44 Traits of Great Early-Stage Sellers
13:00 Does Domain Expertise Matter?
15:28 Best Practices for Sales Onboarding
17:48 Sales Methodologies: MEDDICC & BANT
22:14 Creating Real Urgency in the Sales Cycle
30:23 Value-Based Pricing & Market Signals
38:09 Building a Business Around Open Source
42:16 Sales Methodologies for Founders
43:40 Hiring a CRO: When & What to Look For
You can watch it here or add it to your episodes on Apple or Spotify 🎧 chapters for easy navigation are available on the Spotify/Apple episode.
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Key Takeaways from the Conversation
Start with Hustle, Not Hierarchy
Founders shouldn’t hire a CRO too early — what you really need is a gritty sales rep who can evolve into leadership. Look for hustle, adaptability, and hands-on mentality over polished resumes.
From Startup Hustle to Scale at Speed
Tim shares his journey scaling three companies — Acquia, Project44, and now HAProxy — and why he chooses companies at the $15M inflection point, where early traction meets the opportunity to scale. He explains how the most meaningful GTM roles are about doing the hard work, not just managing it.
He outlines how HAProxy, a bootstrapped and profitable company, grew to 40% YoY growth with no VC backing, proving that excellence in product and GTM alignment can be achieved sustainably.
Focus on Traction, Not Just Revenue
Early sales should prioritize strategic wins: pilots, logos, and learning, not just ARR. Traction is the real early indicator of product-market fit.
Build a Culture, Not a Clone Army
Cultural fit means alignment with the values of the company, not a shared background. Embrace diversity of experience and thought while ensuring buy-in to team norms and expectations.
Surround, Don’t Spam
Modern pipeline-building is about surround tactics: targeted outreach, social engagement, smart tooling (like AI SDRs), ABM campaigns, and high-quality direct mail — all working in concert.
Learn to Qualify with Precision
Salespeople often lose deals because they never meet the economic buyer. Learn to ask: “What has to happen to get this deal done?” and map every stakeholder, step, and timeline with clarity.
Use Frameworks Early — Even as a Founder
Sales methodologies like MEDDIC or BANT aren’t just for big teams. Founders can use them to qualify deals, plan sales strategies, and gain a deeper understanding of buyer psychology.
Open Source: Lead with Community & Content
HAProxy’s model proves the power of open source. The secret? Educating the community, offering real value in enterprise editions, and staying true to product integrity.
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