Overview
You're managing 4-6 SDRs on Rippling's Strategic segment, focused on prospecting into 200-2000+ employee companies. You're a player-coach—carrying a small book of accounts yourself while spending 70% of your time coaching, running 1:1s, and optimizing team performance. You report to Mike Panara Jr. and work hybrid (3 days/week) from SF.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | SDR Manager (Player-Coach) |
| Sales Motion | Managing outbound-heavy team |
| Deal Complexity | N/A (managing team prospecting consultative deals) |
| Sales Cycle | N/A (team books meetings for AEs) |
| Deal Size | N/A (AEs close $50K-250K+ deals) |
| Quota (est.) | Team: 70-100 qualified meetings/month |
Company Context
Stage: Late-stage growth (Series G, $16.8B valuation)
Size: 6,816 employees
Growth: Strategic segment just doubled SDR headcount after strong FY results. You're hiring into a growth motion, not backfilling.
Market Position: Competing against legacy HR/payroll players (ADP, Paychex) and point solutions. Known for unified platform that consolidates 10+ tools.
GTM Reality
Pipeline Sources:
- 20-30% Inbound leads (website, G2, referrals) requiring qualification
- 70-80% Outbound prospecting (cold calls, sequences, LinkedIn)
SDR/AE Structure: Your team feeds Strategic AEs. You're accountable for meeting volume, quality, and conversion rates to accepted opportunities.
SE Support: Strategic deals get SE support in active cycles, but SDRs handle initial outreach solo.
Reporting Structure: You report to Mike Panara Jr. (Senior Director, Sales Development). You'll have 4-6 direct reports initially, likely scaling to 8-10 as team grows.
Competitive Landscape
Main Competitors: ADP, Paychex (legacy), Gusto, BambooHR, Okta, Brex (point solutions), Namely, Paylocity (smaller all-in-one players)
How They Differentiate: True all-in-one platform vs. stitched-together point solutions. Real automation between HR, IT, and Finance.
Your Job: Ensure your SDRs can articulate this value in 30-second cold calls and handle objections about switching costs, risk, and "we already have a solution."
What You'll Actually Do
Time Breakdown
Coaching/1:1s (30%) | Performance Analysis (20%) | Player Work (20%) | Hiring/Recruiting (15%) | Internal Meetings (15%)
Key Activities
- Daily coaching and call reviews: Listening to rep calls, giving real-time feedback, live coaching on objection handling. You're in Gong/Chorus daily reviewing conversations and identifying coaching opportunities.
- 1:1s and performance management: Weekly 1:1s with each rep. Reviewing activity metrics (dials, connects, meetings booked, conversion rates). Having tough conversations when someone's underperforming. Building development plans.
- Sequence and messaging optimization: Testing new subject lines, call scripts, LinkedIn templates. A/B testing what resonates with CFOs vs. VPs of HR. Analyzing what's working across the team and scaling it.
- AE partnership and meeting quality: Meeting weekly with AE counterparts to review meeting quality, conversion rates, and feedback. Handling pushback when AEs say meetings weren't qualified. Defending your team when valid.
- Forecasting and reporting: Building weekly/monthly forecasts for meeting pipeline. Reporting up to Mike on team performance, gaps, and hiring needs. Preparing for QBRs with data.
- Player work (20-30%): You still work 10-15 strategic accounts yourself. Partly to stay sharp, partly because the team needs the extra production. You're expected to book 3-5 meetings/month personally.
The Honest Reality
What's Hard
- Balancing player and coach work: When your reps are struggling, you want to focus on coaching. But you also have your own quota to hit. It's a constant tension, especially end-of-month.
- Managing underperformance: You'll have 1-2 reps at any time who aren't hitting quota. PIPs, tough conversations, eventually letting people go. It's the worst part of the job.
- AE friction on meeting quality: AEs will push back on meetings they think are unqualified. Sometimes they're right, sometimes they're being picky. You're the mediator, which gets exhausting.
- Hiring pressure: You're expected to hire 4 SDRs quickly in a competitive market. Sourcing, interviewing, selling candidates on Rippling while being honest about the grind. Then onboarding them well.
- Metrics scrutiny: Mike and leadership are watching activity metrics closely—dials, connect rate, meeting conversion, opportunity acceptance rate. You need to diagnose problems fast and fix them.
- Hybrid requirement: 3 days/week in office isn't negotiable. If you wanted full remote management, this isn't it.
What Success Looks Like
- Team consistently hits 70-100 qualified meetings/month
- 50%+ of your meetings convert to "Accepted Opportunity" with AEs
- Reps promote to AE roles or other closing positions within 12-18 months (you're building a pipeline of talent)
- You retain top performers and quickly cycle out bottom performers
- Your messaging/sequences become templates for other SDR teams at Rippling
Who Your Team Sells To
Primary Buyers (Your SDRs Target):
- CFOs and VPs of Finance (200-1000 employee companies)
- VPs of HR, People Ops, Talent leaders
- CIOs, IT Directors (for identity/device management)
What They Care About:
- Cost consolidation (paying for 10 separate tools)
- Employee experience (onboarding/offboarding complexity)
- Compliance and audit trails
- Risk of switching payroll/benefits systems
Requirements
- 2+ years managing SDR/BDR teams (they want someone who's done this before)
- Proven track record building and scaling outbound motions
- Experience coaching on cold calling, objection handling, and multi-threaded outreach
- Comfortable with data: analyzing activity metrics, conversion funnels, A/B testing results
- Hybrid schedule: 3 days/week in SF office (non-negotiable)
- Willingness to carry a small book (20-30% player work) while managing
- Experience hiring, onboarding, and ramping SDRs quickly