Head of Sales Recruiting
WinIt
We’re hiring a Sales Enablement Manager to coach our inbound sales team to its best performance. Coaching is the core of this job. You’ll spend most of your week listening to calls, sitting with reps, and running coaching sessions. Then you’ll turn what you learn into training, scripts, and playbooks that lift the whole team. What you’ll do
Listen to and score calls every day, and give each rep specific, actionable feedback
Run weekly one-on-one coaching sessions with every rep, with clear goals and follow-up
Build individual development plans based on each rep’s call data and skill gaps
Lead live call shadowing and side-by-side coaching, and jump in to model great calls yourself
Run team call reviews, where reps break down winning and losing calls together
Run regular role-plays on discovery, objection handling, pricing conversations, and closing
Coach top performers to get even better, not just struggling reps
Train team leads and managers to coach well, so coaching scales beyond you
Build a coaching cadence and scorecard so every rep knows what “good” sounds like
Own new-hire onboarding and ramp, including certification calls before reps go live
Build and maintain call scripts, playbooks, and talk tracks for inbound B2C sales
Track KPIs (conversion rate, close rate, average order value, talk time), and show how coaching moves each one
Use call recording and conversation intelligence tools to spot trends and coaching opportunities
What you bring
- 6–7 years of experience in B2C sales, with at least 3 years spent directly coaching or training sales reps
- A proven record of coaching reps to measurably higher conversion in an inbound or high-volume consumer sales team
- Deep experience in call coaching and call QA, plus a sharp ear for what wins and loses a call
- A coaching style that’s direct, encouraging, and consistent, and that makes reps seek out your feedback
- Experience training managers or team leads to coach their own teams
- Comfort with CRM and call tools (Close, Salesforce, HubSpot, Gong, or similar)
- A data-driven approach: you measure what your coaching changes
- Experience in legal services, insurance, financial services, or another regulated consumer industry is a plus
- Spanish fluency is a plus
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