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.
Frequently asked questions
What part of sales can automation not replace?
Building trust with a buyer. Todd Jenkins, Head of Sales at Airspeed, argues from over a decade leading enterprise deals that frameworks such as MEDDPICC and SPICED give a call structure, but running them as a checklist kills the conversation. Use the structure and stay in the room.
What does Todd Jenkins look for when coaching sales reps?
Coachability, emotional security, and a growth mindset. From there the work is diagnosis, finding the root cause of underperformance before prescribing a fix, confidence, giving reps a safe space to try things and learn from a miss, and honesty about fit, because sales is not for everyone.
How do you make outbound land when every competitor has AI?
Personalize for real by researching the prospect and showing you did the work, count meetings booked rather than volume sent, and use short recorded video to build rapport. Automation makes outreach faster. It does not make it land.
