A few years in B2B SaaS and it’s easy to start treating sales as a tooling problem. In a recent interview on timbertalks, Todd Jenkins, Head of Sales at Airspeed, makes the opposite case: the work that wins deals is still human.
Drawing on over a decade leading enterprise deals and high-performing teams, Todd lands on three things.
Build a real connection
Frameworks like MEDDPICC and SPICED give a call structure. Run them as a checklist and you kill the conversation. Todd’s point: use the structure, but stay in the room. Understand the prospect’s problem, earn their trust, and make it obvious you actually want to help.
Coach the right people, and know when to stop
Good coaching starts with the rep, not the dashboard. Todd looks for coachability, emotional security, and a growth mindset, then works on:
- Diagnosis: find the root cause of underperformance before prescribing a fix.
- Confidence: give reps a safe space to try things and learn from a miss.
- Honesty about fit: sales isn’t for everyone, and the kind move is helping someone find the role that is.
Outbound when everyone has AI
Automation makes outreach faster. It does not make it land. Todd’s advice for cutting through:
- Personalize for real: research the prospect, tailor the message, show you did the work.
- Count the meetings booked: quality conversations are the signal, not volume sent.
- Use video: a short recorded message builds rapport and stands out in a full inbox.
The takeaway
Tools keep changing; what decides the deal does not. Todd’s read is that the human element still wins. Make a genuine connection, build a team that grows, and run outbound with effort rather than templates, and you hold up in any market.
