Sales Development Representative (SDR) - Strategic Segment

Overview

You're an SDR on Rippling's Strategic segment, prospecting into companies with 200-2000+ employees. You book meetings for AEs who sell Rippling's full platform (HR, IT, Finance) to replace fragmented tech stacks. You report to Mike Panara Jr. and work 3 days/week from the SF office.

Role Snapshot

Company Context

Stage: Late-stage growth (Series G, $16.8B valuation, $500M+ raised)

Size: 6,816 employees

Growth: Just doubled Strategic SDR headcount (hiring 4 SDRs + 1 manager). Recent Series G suggests strong growth momentum despite crowded HR tech market.

Market Position: Category challenger - competing against legacy players (ADP, Paychex) and point solutions (Gusto, BambooHR, Okta). Known for being the "all-in-one" platform that actually delivers on the promise.

GTM Reality

Pipeline Sources:

• 20-30% Inbound - product-qualified leads from their website, G2 traffic, referrals. These are warmer but still require multi-touch nurture.
• 70-80% Outbound - cold calling, LinkedIn prospecting, email sequences into target accounts. You're building lists and breaking into companies cold.

SDR/AE Structure: Dedicated SDR team feeding Strategic AEs. You don't close deals—you book qualified meetings and hand off.

SE Support: Strategic deals get SE support once in active cycle, but not on initial calls.

Competitive Landscape

Main Competitors:

• Legacy: ADP, Paychex (established, expensive, clunky)
• Point solutions: Gusto (payroll), BambooHR (HR), Okta (IT), Brex (finance)
• All-in-one: Namely, Paylocity (smaller players)

How They Differentiate: Single platform for HR, IT, and Finance vs. stitching together 10+ tools. Real automation between systems (offboard someone → revoke all app access automatically).

Common Objections:

• "We already have ADP/Paychex and it works fine"
• "Switching payroll is too risky mid-year"
• "We prefer best-of-breed tools"
• "Too expensive vs. our current setup"

Win Themes: ROI from consolidation, automation that actually works, better employee experience, unified data.

What You'll Actually Do

Time Breakdown

Prospecting (50%) | Lead Follow-up (25%) | Research/Admin (15%) | Internal Meetings (10%)

Key Activities

• Cold calling into target accounts: 60-80 dials/day to CFOs, VPs of HR, IT Directors, Finance leaders. You're interrupting their day to explain why they should consolidate systems. Most calls go to voicemail. You need thick skin.
• Multi-threaded outreach sequences: Building lists of 3-5 contacts per account, hitting them with coordinated emails, LinkedIn touches, and calls over 2-3 weeks. Tracking everything in Salesforce/Outreach.
• Discovery on inbound leads: When someone fills out a form, you call within 5 minutes to qualify them (company size, current tools, buying timeline, budget authority). Many are tire-kickers or too small for Strategic.
• Meeting prep and handoff: Writing detailed meeting notes for AEs—company background, pain points discovered, stakeholders identified, competitive intel. If you pass garbage meetings, AEs will let you know.

The Honest Reality

What's Hard

• Gatekeepers and voicemail: You'll leave 50+ voicemails per day. Assistants are trained to block you. Getting a live conversation with a VP is a win in itself.
• Long nurture cycles: Even when someone's interested, they're not buying today. You're planting seeds for deals that close 6 months later. Hard to see immediate impact.
• Competitive noise: Every HR tech vendor is calling the same people. You're competing for attention against Deel, Gusto, ADP reps, and 10 other SDRs that week.
• Hybrid requirement: 3 days/week in SF office isn't flexible. If you wanted full remote, this isn't it.
• Meeting quality scrutiny: AEs will push back if your meetings aren't qualified. You need to actually discover pain and confirm budget/authority, not just book any meeting to hit quota.

What Success Looks Like

• Hit 12-18 qualified meeting quota monthly (meetings that show up, have real pain, and progress to next stage)
• 50%+ of your meetings convert to "Accepted Opportunity" status with the AE team
• Build a pipeline of nurture accounts that turn into meetings in 30-90 days
• Promote to Strategic AE role or move into closing within 12-18 months (career path exists here)

Who You're Selling To

Primary Buyers:

• CFOs and VPs of Finance (200-1000 employee companies)
• VPs of HR and People Ops
• CIOs, IT Directors (identity/device management angle)

What They Care About:

• Cost consolidation: Paying for 10 different tools is expensive and hard to manage
• Employee experience: Current onboarding/offboarding is clunky, too many logins
• Compliance and security: Need audit trails, SOC 2, data accuracy across systems
• Switching risk: Terrified of payroll/benefits migration going wrong

Requirements

• 1+ year of SDR/BDR experience (they want people who know the grind)
• Comfortable cold calling senior executives (VPs, C-level)
• Able to work hybrid schedule: 3 days/week in SF office
• Familiarity with Salesforce, Outreach/Salesloft, LinkedIn Sales Navigator
• Ability to learn complex product (HR + IT + Finance platform) and articulate value quickly
• Coachable and metrics-driven—this team has structure and expectations