How do you scale a SaaS sales org from $2M to $10M in ARR without losing momentum—or your mind?

Peter Crosby, Chief Commercial Officer at Triptease, joins Dimitar to break down:

• What changes (and what doesn’t) as you move from early traction to real scale

• How to build the right sales motion for your growth stage

• Mistakes to avoid when hiring, structuring, and forecasting

• How Triptease navigated this critical growth window

If you're scaling a SaaS business, this episode is a roadmap for the messy middle.

What does it take to launch and scale the European arm of a hypergrowth US tech company?

Dimitar sits down with James Parton, Twilio’s former Director of Europe, to talk about:

• The early days of Twilio’s expansion across Europe

• How “developer-led” sales really works

• The role of pre-sales, sales engineering, and enablement in technical GTM

• What it's like being the first boots on the ground for a US startup abroad

A must-listen for anyone scaling international teams or building go-to-market in dev-first businesses.

What do Just Eat, Funding Circle, GoCardless, and Property Partner have in common? They all turned to Terry Russell to help scale their sales teams.

In this episode, Terry shares:

• How to design comp plans that actually motivate

• The secret to developing sales talent in fast-growing orgs

• Hard-won lessons from inside some of Europe’s best-known startups

Whether you’re a founder, sales leader, or coach yourself, Terry’s stories are full of practical takeaways you can apply right away.

What changes when a company goes from private to public? Alan Kenny, GM Europe at Mimecast, shares the hard-earned sales lessons that rarely get talked about.

We dig into:

• What salespeople and managers really need to know during hypergrowth

• The leadership mistakes Alan would go back and fix

• How to stay effective as the org scales and complexity kicks in

• Practical advice for navigating growth from startup to IPO

If you're in SaaS sales or sales leadership, this one's full of sharp, experience-backed insights.

Just days before Atlassian’s $425M acquisition of Trello, we sat down with Kristen Habacht, VP of Sales, to unpack what it really takes to build and scale a freemium SaaS sales org.

We cover:

• How Trello’s sales team evolved from full-stack to role specialization

• Why they simplified their commission structure

• The realities of selling a freemium product—and why BANT doesn’t work

• Managing remote sales teams long before it was the norm

• What Kristen wishes she knew earlier

Whether you’re running SMB, enterprise, or product-led GTM, this episode is packed with battle-tested insights from one of SaaS’s most interesting growth stories.

==============================================================Music credits: - Intro - Qvkata DLG, Duis Taban- Outro - Victor Hugo