Note: The job is a remote job and is open to candidates in USA. Wing Assistant is seeking a Sales Pipeline Lead to enhance their sales process and ensure deals do not stall. The role involves monitoring sales activity, directly engaging with prospects, coaching AEs, and reporting on pipeline health to improve conversion rates.
Responsibilities
- 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
Skills
- 3-5 years of B2B sales experience with a track record of personally closing deals, not just managing a pipeline from a distance
- 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
- Strong phone presence and objection handling skills
- Assertive but collaborative working style
- High urgency
- Analytical mindset
- 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
Company Overview