Outbound SDR - NAM

Overview

You make 60-80 cold calls per day to HR directors, CFOs, and IT managers at small-to-mid-sized companies (typically 50-500 employees) across North America. Your job is to book qualified demos for Account Executives who sell Rippling's unified HR, payroll, benefits, IT management, and spend management platform. You're selling against the status quo—most prospects are using ADP or Gusto for payroll, BambooHR for HRIS, Okta for IT, and don't realize they could consolidate.

Role Snapshot

Company Context

Stage: Series D+ / Late-stage (valued at $11B+ as of last raise)

Size: ~3,000 employees

Growth: Aggressive hiring across sales, expanding from HR tech into finance/IT/spend management

Market Position: Category consolidator in a fragmented market—competing against established HR platforms (ADP, Workday, BambooHR), payroll providers (Gusto), and IT tools (Okta, Jamf)

GTM Reality

Pipeline Sources:

• 80% Outbound - Cold calls to HR/finance leaders, targeted LinkedIn outreach, email sequences to companies in expansion/hiring mode
• 15% Inbound - Website form fills from content downloads, comparison searches ("Rippling vs Gusto"), product review sites
• 5% Referrals - Customer references, broker partnerships

SDR/AE Structure: Dedicated SDRs feed named AEs. You own outbound prospecting; AEs handle inbound leads themselves and work the demos you book.

SE Support: AEs have access to solutions engineers for complex demos, but initial discovery calls are AE-only.

Competitive Landscape

Main Competitors:

• ADP, Paychex (legacy payroll)
• Gusto, Justworks (SMB all-in-one)
• BambooHR, Workday (HRIS)
• Okta, Google Workspace (IT management)

How They Differentiate: Single platform that does HR, payroll, benefits, device management, app provisioning, and corporate cards—versus juggling 5-8 point solutions. The pitch is operational efficiency and data consolidation.

Common Objections:

• "We just implemented [ADP/BambooHR/Gusto] 6 months ago"
• "Switching payroll is too risky"
• "Our IT team won't give up Okta"
• "We're too small to need all these features"

Win Themes: Companies in growth mode (recently raised funding, expanding headcount) who are tired of logging into 8 systems and manually syncing data between HR, IT, and finance tools.

What You'll Actually Do

Time Breakdown

Cold Calling (50%) | Email/LinkedIn (25%) | Research/List Building (15%) | Internal Meetings (10%)

Key Activities

• Cold Calling (60-80 dials/day): Calling HR directors, CFOs, and heads of people ops. Most calls go to voicemail. You're trying to catch someone between meetings who admits they're frustrated with their current payroll/HR stack. Goal is 2-3 live conversations per day.
• Email Sequences: Running automated cadences through Outreach or Salesloft. Personalizing first lines based on recent funding rounds, job postings, or tech stack research (e.g., "saw you're using Gusto + BambooHR + Expensify—what if one platform did all three?").
• Discovery/Qualification: When you get someone on the phone, you're asking about current vendors, employee count, pain points with data sync issues or manual processes. Qualifying for budget authority and timeline before passing to AE.
• CRM Hygiene: Logging every call, email, and interaction in Salesforce. SDR managers track activity metrics closely—calls made, emails sent, connect rate, meeting conversion rate.

The Honest Reality

What's Hard

• High rejection volume: Most people don't pick up. Of those who do, many say "we're happy with our current setup" or "not the right time." You'll hear "no" 50+ times per day.
• Long buying cycles downstream: Even when you book a meeting, deals often take 3-6 months to close (payroll migrations happen at year-end or quarter-end). You won't see immediate results from your pipeline.
• Competing against inertia: Rippling is objectively better than using 5 separate tools, but switching payroll/HR systems is a massive project. Prospects need to be in real pain to move.
• Crowded market: Everyone's heard of ADP, Gusto, or Workday. Rippling is well-known in tech circles but you're still educating buyers in traditional industries.

What Success Looks Like

• Booking 12-15 qualified meetings per month (meetings that show up and have decision-making authority)
• 8-10% connect rate on cold calls (80 dials → 6-8 conversations)
• 30%+ of your booked meetings converting to active opportunities for AEs
• Promoting to AE within 12-18 months if you hit quota consistently

Who You're Selling To

Primary Buyers:

• VP/Director of HR or Head of People (50-500 person companies)
• CFO or Finance Director (at smaller companies where finance owns payroll)
• IT Director or Head of IT (when selling device/app management angle)

What They Care About:

• Reducing manual work (tired of entering employee data into 5 systems)
• Payroll accuracy and compliance (current provider makes mistakes)
• Onboarding/offboarding efficiency (provisioning laptops, apps, and benefits in one flow)
• Reporting/analytics (want unified people data, not spreadsheets)
• Cost consolidation (paying for Gusto + BambooHR + Okta + Expensify adds up)

Requirements

• Comfortable making 60-80 cold calls per day and hearing "no" constantly
• Ability to research companies (funding news, job postings, tech stack) to personalize outreach
• Coachable—Rippling has a structured SDR training program and expects you to follow their playbook
• Competitive and metrics-driven (you'll be ranked on a leaderboard weekly)
• 1-2 years in a customer-facing role preferred but not required (they hire and train hungry entry-level reps)