Mastering Sales Onboarding

In this new episode of Path to Market, our Director

and co-host

, Partner at Pipeline Ventures, sit down with

— 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

, Tim previously held sales leadership roles at

and

, 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