About the Role
Every deal in our pipeline represents a prospect who raised their hand and said they're interested. Too many of those deals are dying — not because the prospect said no, but because we lost momentum. Follow-ups get delayed, next steps go stale, AEs get busy with new demos and forget to circle back, and deals that should have closed quietly slip away.
The Sales Pipeline Lead exists to make sure that stops happening. You are a player-coach who lives inside Pipedrive, monitors every active deal across all three sales squads, and personally intervenes when deals start stalling. You call prospects directly. You jump on calls with AEs. You catch deals that are scoped wrong before they close and create problems downstream. You hold AEs accountable for follow-up cadence and pipeline hygiene — not through reports, but by being in the pipeline with them daily.
Responsibilities
What You'll Do
Monitor Pipedrive daily across all three sales squads. Identify deals that are stalling, aging past expected timelines, or missing recent activity. Take action the same day — not next week.
Personally intervene on stalling deals. Call prospects directly to re-engage. Re-frame the value proposition. Address objections the AE couldn't overcome. Join AE calls when a second voice or senior presence could move the deal forward.
Hold AEs accountable for follow-up cadence. Every qualified deal should have a defined next step and a recent touchpoint. If an AE has a deal sitting untouched for 48+ hours, you flag it immediately and ensure action is taken.
Catch incorrectly scoped deals before they close. Review deals approaching close to verify the prospect is on the right plan, the expectations are set correctly, and the deal won't create problems post-sale. If something is off, intervene before it closes — not after.
Coordinate with the Solutions Expert to warm hesitant prospects. When a prospect is interested but not yet convinced, arrange pre-close work extraction or other value demonstrations that show them what working with Wing actually looks like.
Run weekly pipeline health reports. Report to leadership on conversion rates by stage and by AE, deal velocity, deals rescued, deals lost and why, and patterns in pipeline fall-through. Identify systemic issues and recommend fixes.
Coach AEs on deal management. This is not classroom training — it's in-the-moment coaching. After you rescue a deal, walk the AE through what happened and what they should do differently next time. Your goal is to make yourself less needed over time.
Requirements
What You'll Need
3-5 years of B2B sales experience with a track record of personally closing deals, not just managing a pipeline from a distance. You know how to pick up the phone and move a deal forward.
Experience in a player-coach or senior AE role where you were responsible for both your own deals and helping others close theirs.
Deep comfort with CRM systems — Pipedrive strongly preferred. You should be able to read a pipeline view and immediately identify which deals need attention without someone telling you.
Strong phone presence and objection handling skills. You will be talking to prospects daily — often prospects who have gone cold or are hesitating.
Assertive but collaborative working style. You need to hold AEs accountable without creating friction. You're their coach, not their adversary.
High urgency. Deals die from delay. You operate with a same-day mentality — if something needs attention, it gets attention now.
Analytical mindset. You can spot patterns in pipeline data: which stages are leaking, which AEs are struggling, which lead sources produce deals that stall.
Nice to Have
Experience in virtual staffing, SaaS or managed services industry.
Familiarity with Pipedrive reporting and automation features.
Track record of improving pipeline conversion rates in a previous role.
Experience working alongside Solutions Engineers, Solutions Experts, or pre-sale technical resources.
Similar Jobs
What you need to know about the Boston Tech Scene
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories
