Why "Just Checking In" Is Killing Your Pipeline (And What to Do)
Most B2B sales cycles are brutally long, but sales teams don't know how to stay present without being annoying. Jason breaks down how to create milestone moments — legitimate, value-led reasons to reach out — using owned media.
Most B2B sales cycles are brutally long, but sales teams don’t know how to stay present without being annoying. The traditional approach fails — discovery call, proposal sent, then “just checking in” emails with no response.
Jason’s core point is clear: 95% of B2B Better’s clients have sales cycles over six months. And 95% of your customers are out of market at any given time. Your job is to stay present so when they flip to being in market, they think of you first.
Milestone moments fix this. Month one: send proposal plus a podcast clip addressing their exact challenge. Month three: benchmark report. Month four: webinar invite. Month five: customer story. Month six: check in with context. Months seven to twelve: new episodes create new reasons to reach out. Month eighteen: deal closes because you felt like a partner.
B2B Better’s sales enablement kits deliver three clips with email copy, key graphics, follow-up sequences, and tags showing which funnel stage each piece serves. One innovation: sales stitch videos where reps record 30-second reactions to clips. Personal brands beat company brands — these generate thousands of views when originals get hundreds.
Key Takeaways
- Why “just checking in” emails signal you have nothing valuable to say — and what to send instead.
- How milestone moments create legitimate, value-led reasons to reach out across 6–12 month sales cycles.
- What a full 18-month milestone roadmap looks like in practice — from proposal to closed-won.
- How to build sales enablement kits from podcast content — clips, email copy, graphics, and funnel-stage tags.
- Why sales stitch videos generate more views than original content — and how to brief your reps to create them.
- The three requirements for this to work: marketing-sales alignment, shared infrastructure, and CRM attribution.
Chapter Markers
- 00:00 The “just checking in” problem that kills deals
- 01:00 Context on long sales cycles and 95% out-of-market buyers
- 02:00 Why owned media strategies fall apart at sales activation
- 03:00 Traditional approach: proposal to dead deal in 12 months
- 04:00 Milestone moments approach: 18-month cycle done right
- 06:00 What qualifies as a milestone moment
- 07:00 Timing and sequencing content to the buyer journey
- 08:00 Sales enablement kit components
- 09:00 Tags and metadata for searchable, attributable content
- 10:00 Sales stitch videos: personalising content at scale
- 12:00 Three requirements: alignment between teams
- 14:00 Attribution: quantitative and qualitative tracking
