MidMarket Account Executive

Overview

You sell Rippling's all-in-one employee management platform to mid-market companies (50-500 employees), replacing their patchwork of HR, IT, and payroll tools. You run full-cycle deals from demo to close, typically juggling 15-25 active opportunities. You're in the office 3 days per week in SF, NYC, or Austin, spending the rest of your time on Zoom with prospects across North America.

Role Snapshot

Company Context

Stage: Series D+ / Late-stage growth (Valued at $13.5B+ as of last funding)

Size: 3,000+ employees

Growth: Aggressively hiring across all GTM teams, frequent internal promotions mentioned in post

Market Position: Category challenger/disruptor - competing against established players (Gusto, BambooHR, Workday, ADP) with a unified platform approach that consolidates HR, IT, and Finance tools

GTM Reality

Pipeline Sources:

• 50% Inbound - Mix of demo requests from website, content downloads, referrals. Quality varies—some are ready to buy, others are early research mode or tire-kickers comparing 5+ vendors
• 40% Self-sourced - You build your own pipeline through LinkedIn outreach, referrals from closed deals, and working old opportunities that went cold
• 10% SDR-generated - Shared SDR pool books initial discovery calls, but you do most of your own prospecting

SDR/AE Structure: Shared SDR pool, but top reps self-source 60%+ of their pipeline

SE Support: Shared SE pool for complex demos (integrations, custom workflows), but you run most standard demos solo

Competitive Landscape

Main Competitors: Gusto (payroll/HR), BambooHR (HR), Workday (enterprise HR), ADP/Paychex (payroll), plus point solutions like Okta, Jamf, Expensify

How They Differentiate: Single platform for HR, IT, Finance vs. best-of-breed tools. Key pitch: "One system of record, automatic data sync, no integrations to break." Workflow automation is a major differentiator.

Common Objections: "We already have [Gusto/BambooHR] and it works fine," "Switching tools is too disruptive," "We prefer best-of-breed," "Implementation seems complex," pricing concerns for smaller companies

Win Themes: Companies tired of managing 8-12 disconnected tools, integration headaches, manual data entry between systems, and scaling pains as they grow

What You'll Actually Do

Time Breakdown

Active Deals (45%) | Prospecting (30%) | Internal Stuff (25%)

Key Activities

• Running product demos: You give 5-8 demos per week, walking prospects through the platform. Standard demo is 45-60 minutes. You tailor it to their stack—showing how Rippling replaces their current HR tool, IT management, and expense system. You'll screen-share, click through workflows, answer "can it do X?" questions on the fly.
• Multi-threading deals: You're not just talking to HR. You need to loop in IT (device management), Finance (expense/bill pay), and often the CEO or CFO for final approval. You spend hours coordinating 3-way calls, sending follow-up materials to different stakeholders, and managing group consensus.
• Chasing next steps: Deals stall constantly. Prospects go dark after the demo, or they say "we need two more weeks" which turns into two months. You send follow-up emails, LinkedIn messages, and text reminders trying to get them to schedule the next call or send over their current contract for comparison.
• Building your own pipeline: You spend 1-2 hours daily on LinkedIn, reaching out to VPs of HR or Finance at companies in your ICP range. You also ask closed customers for referrals and work old leads that didn't convert 6-12 months ago.
• Internal coordination: Weekly forecast calls, deal reviews with your manager, Slack threads with SEs and implementation teams, entering notes in Salesforce. You also spend time in product training sessions learning new feature releases (Rippling ships fast).

The Honest Reality

What's Hard

• Long decision cycles: Even though the sales cycle is "60-90 days," plenty of deals stretch to 4-6 months. You're dealing with change management—switching core systems is scary for companies. Budget approval often requires CFO sign-off, which adds weeks. You'll have deals you thought were closing this month slip to next quarter.
• Competitive market: You're going up against entrenched vendors. Gusto has strong SMB brand recognition. BambooHR loyalists don't want to switch. You lose deals to "status quo" constantly—prospects decide the pain of switching isn't worth it, even if they like your product.
• Complex deals with lots of moving parts: You're not selling a single product. You're replacing 5-10 tools. This means more stakeholders, more objections, more "we need to check with IT/Finance/Legal" delays. Implementation concerns come up in every deal. You need to project-manage the entire sales process.

What Success Looks Like

• Hitting $1M+ per year in closed revenue: Top reps close $1.2-1.5M annually and make $500K+ total comp
• Maintaining 25+ active opportunities: If your pipeline drops below 20 deals, you're not prospecting enough
• 4-6 deals closed per quarter: Avg deal size $40-60K ACV, so you need consistent velocity

Who You're Selling To

Primary Buyers:

• VP of HR / Head of People (companies with 100-500 employees)
• VP of Finance / CFO (for bill pay, expense management, and budget approval)
• VP of IT / Head of IT (for device management and app provisioning)
• CEO/Founder (at smaller end of range, 50-150 employees)

What They Care About:

• Reducing tool sprawl and admin burden: Tired of logging into 8 systems, manual data entry, and broken integrations
• Time savings on onboarding/offboarding: Automating laptop orders, app access, payroll setup in one workflow
• Compliance and audit trails: Need to prove they're handling employee data correctly, especially with SOC 2 or other certifications
• Scalability: Current tools are breaking as they grow—need something that works at 500+ employees without a rip-and-replace
• Cost: They'll compare total cost vs. their current stack. Rippling isn't always cheaper upfront but you sell time savings.

Requirements

• 3+ years of full-cycle B2B SaaS sales experience (mid-market or enterprise)
• Track record of closing $50K+ ACV deals with 60-90 day sales cycles
• Experience selling to HR, Finance, or IT buyers (ideally multi-stakeholder deals)
• Comfortable running your own product demos and self-sourcing 50%+ of pipeline
• Based in or willing to relocate to SF, NYC, or Austin with 3 days/week in-office
• Ability to handle 15-25 concurrent deals without dropping the ball