From Plumber to Sales Leader: Managing Modern Mid-Market Deals - Superior

Haydon Zaccaria, UK Sales Manager at Tipalti, joins the Revenue Revolution Podcast to share his journey into SaaS sales and how he manages modern mid-market deals.

He explains what has changed in B2B buying, why deals stall, and how sales leaders can coach teams to perform consistently in more complex environments.

From Plumber to SaaS Sales Leader

Haydon did not start his career in software. After a semi-professional football career ended early, he worked as a plumber before moving into recruitment and eventually SaaS sales.

"Plumber to President's Club."

That experience shaped his resilience and perspective. Manual labour taught him discipline, consistency, and the ability to push through difficult days, skills he still draws on in sales leadership.

Why Mid-Market Sales Now Feels Like Enterprise

Mid-market deals have become significantly more complex.

"I think a lot of enterprise process is coming downstream into the mid-market."

Buyers now involve more stakeholders, legal reviews, and security discussions. Accountability is spread across teams to reduce individual risk, increasing deal complexity and length.

As a result, mid-market teams must adopt a more enterprise-style approach to deal management.

How to De-Risk the Buying Decision

Buyers today are driven more by fear of failure than fear of missing out.

"People are more afraid of messing up."

To address this, Haydon focuses on bringing post-sales clarity into pre-sales conversations. Explaining onboarding, implementation, and long-term success early helps buyers feel safer committing to a decision.

Why Poor Qualification Causes Deals to Stall

Most stuck deals can be traced back to weak qualification.

"How do you get out of a rear naked choke? Don’t get in to start with."

Proper qualification means identifying a true champion, understanding the route to signature, and avoiding deals where influence or authority is missing from the outset.

How Haydon Coaches Reps to Qualify Better

Strong qualification requires active coaching, not just frameworks.

Haydon invests heavily in post-mortems, deal reviews, and one-to-one coaching to help reps improve over time. The goal is to move reps toward unconscious competence, where qualification feels natural and conversational.

"Just relax... Just try and sound like yourself."

Why Internal and External Multi-Threading Matters

Multi-threading is just as important internally as it is externally.

"I think it's equally as important, if not more important, to multi-thread internally."

Strong relationships with solutions consultants, onboarding, and leadership reduce friction and make it easier to move deals forward. Externally, proactive guidance ensures the right stakeholders are involved at the right time.

The Sales Metrics That Matter Most

Haydon challenges activity-based metrics like raw dial counts.

"Dials for dials' sake."

Instead, he prefers fewer accounts with deeper engagement, measuring success through account penetration and stakeholder involvement rather than volume alone.

How AI Will Change the Future of Selling

Haydon sees AI as an amplifier of top performers.

By removing admin and automating low-value tasks, AI will allow strong sellers to operate at a much higher level, creating fewer but more powerful AEs.