SDR - Global Cross-Sell Team

Overview

You work on Rippling's Global Cross-Sell team, prospecting into existing customers to find expansion opportunities. Your job is to identify companies already using some Rippling products (maybe just payroll, or just HRIS) and book meetings for AEs to sell them additional modules (IT management, benefits admin, finance tools, etc.). You're not cold calling strangers—you're researching accounts that already have a relationship with Rippling and finding the right stakeholders who need solutions they're not using yet.

Role Snapshot

Company Context

Stage: Late-stage, well-funded private company (raised $1B+ at $13.5B valuation in recent rounds)

Size: 7,000+ employees

Growth: Aggressive expansion—they're adding headcount fast and pushing hard into cross-sell motion

Market Position: Category leader in unified workforce management—competing with point solutions (Gusto, ADP, Workday, Okta, etc.) by being an all-in-one platform

GTM Reality

Pipeline Sources:

• 100% Outbound to existing customers—you're given a book of accounts already using Rippling and you're identifying whitespace
• Some inbound leads from customer success flagging expansion opportunities, but you're mostly self-sourcing

SDR/AE Structure: You work directly with assigned AEs on the cross-sell team. You book meetings, they take them and close.

SE Support: AEs likely have SE support for technical demos, but you're not involved in that—you just need to understand the product well enough to have credible conversations about pain points.

Competitive Landscape

Main Competitors: Point solutions in each category—Gusto/ADP for payroll, BambooHR/Workday for HRIS, Okta/JumpCloud for IT management, Brex/Ramp for finance tools

How They Differentiate: "One platform instead of stitching together 5-10 tools"—sell efficiency, data consistency, and eliminating manual integrations

Common Objections:

• "We just signed a 3-year contract with [incumbent]"
• "Our IT team is happy with Okta, why switch?"
• "This sounds expensive to implement"
• "We don't have bandwidth for a migration right now"

Win Themes: Companies frustrated by tool sprawl, manual data entry between systems, or paying for redundant features across multiple platforms

What You'll Actually Do

Time Breakdown

Research/Account Planning (25%) | Outreach (50%) | Meetings/Handoffs (15%) | Internal Syncs (10%)

Key Activities

• Account Research: You review which Rippling products each account is currently using, look at company size/growth, check LinkedIn for relevant stakeholders (CFO, CHRO, IT Director), and identify which modules they're NOT using that would be relevant
• Outbound Outreach: Cold calling and emailing into accounts—these aren't totally cold since they're Rippling customers, but the specific person you're reaching probably doesn't know you. You're making 40-60 calls/day and sending 30-40 personalized emails trying to get someone on the phone or book a meeting
• Discovery Conversations: When you get someone live, you're qualifying pain points around the modules they're not using. "I see you're using Rippling for payroll but managing IT through Okta—how's that integration working?" You need to uncover enough pain to hand off a qualified meeting
• Meeting Handoffs: You book meetings for AEs, join the first 5-10 minutes to do intros and context, then drop off. You're measured on whether the meeting shows up and if the AE accepts it as qualified

The Honest Reality

What's Hard

• Gatekeeping: Even though the company uses Rippling, getting to decision-makers in other departments is tough. You're calling the finance team about IT tools or the IT team about finance tools—they don't know you and may not care
• Competing Priorities: Customers are dealing with their day jobs. Getting them to take a meeting about expanding into a new module when everything is "working fine" requires persistence and catching them at the right moment
• Long Research Cycles: You can't just blast generic messages—you need to understand what they're currently using, research the stakeholders, and craft relevant outreach. This takes time and you're still expected to hit high activity numbers
• Pipeline Churn: Accounts go dark, priorities shift, budget freezes happen. Your carefully nurtured prospect suddenly stops responding

What Success Looks Like

• 15-25 qualified meetings booked per month (meetings where the AE agrees the prospect has real pain and budget)
• High show rate (80%+ of booked meetings actually happen)
• Consistent activity: 40-60 calls/day, 30-40 emails/day, strong pipeline coverage
• AE feedback: Your meetings convert to opportunities at a reasonable rate

Who You're Selling To

Primary Buyers:

• CFOs, Controllers, Finance Directors (for finance/expense management modules)
• CHROs, VP HR, HR Directors (for benefits, performance management, recruiting modules)
• CIOs, IT Directors, IT Managers (for device management, app provisioning, security tools)

What They Care About:

• Efficiency: Reducing manual work, eliminating double-entry between systems
• Cost: Consolidating vendors, reducing tool sprawl
• Data accuracy: Single source of truth for employee data
• Implementation burden: How painful is it to migrate/onboard a new module?

Requirements

• 1-2 years of SDR/BDR experience (or strong entry-level candidate with grit)
• Comfortable with high call volume and rejection
• Ability to learn complex product suite quickly—you need to understand 8-10 different product modules well enough to have credible conversations
• Self-starter who can manage their own book of accounts and prioritize outreach
• Must be based in Austin, NYC, or San Francisco (no remote)
• Competitive mindset—cross-sell SDR teams tend to be leaderboard-driven