Account Executive

Overview

You're selling Bolto—a consolidated recruiting, payroll, and HR platform—to startups and fast-growing companies that are juggling Greenhouse + Gusto + BambooHR (or similar). Your job is to find companies outgrowing their patchwork setup, run demos showing how Bolto consolidates everything, and close deals where you're typically displacing 2-3 incumbent vendors. Most of your conversations are with Heads of People, HR Directors, or founders at 20-200 person companies.

Role Snapshot

Company Context

Stage: YC-backed seed stage (15 employees)

Size: 15 people total

Growth: Recently doubled team size, actively hiring across multiple roles

Market Position: New entrant in a crowded HR tech space—competing against established point solutions and newer all-in-one platforms like Rippling and Deel

GTM Reality

Pipeline Sources:

• 30% Inbound - mostly website demos from companies researching "all-in-one HR platform" or landing via YC network
• 60% Outbound - cold outreach to HR leaders at funded startups, companies in growth stage (Series A-C)
• 10% Referrals - YC network, customer referrals

SDR/AE Structure: No dedicated SDR team yet—you're doing your own prospecting

SE Support: Likely founder-led or shared eng resources for technical questions, no dedicated SE

Competitive Landscape

Main Competitors: Rippling (800-lb gorilla), Deel (global focus), Gusto + Greenhouse + BambooHR combo (status quo)

How They Differentiate: AI-powered compliance automation, tighter integration since it's purpose-built as one platform vs acquisitions stitched together

Common Objections: "We already have [Gusto/Rippling]", "Too early-stage/unproven", "Migration sounds painful", "What if you get acquired or shut down?"

Win Themes: Actually consolidated (not just bundled), better UX than legacy tools, faster implementation than Rippling, AI saves time on compliance busy work

What You'll Actually Do

Time Breakdown

Prospecting (40%) | Active Deals (35%) | Internal/Admin (25%)

Key Activities

• Prospecting: Send 50-75 personalized emails per week to HR leaders at funded startups. Use LinkedIn, Crunchbase, and YC directories to find companies in growth mode. Most won't respond. You're looking for companies at inflection points—just raised a round, hiring aggressively, or complaining about their current tools on Twitter.
• Discovery Calls: Run 30-45 min calls to understand their current stack, pain points, and buying timeline. You're qualifying whether they have budget, authority, and genuine pain. Half of these go nowhere because they're just researching or not actually ready to switch.
• Product Demos: Walk through Bolto's recruiting, payroll, and HR modules in 45-60 min demos. You'll get questions about integrations, compliance in specific states, and how migration works. Technical questions you can't answer go to the founders or eng team.
• Deal Management: Chase stakeholders for next steps. Most deals involve the HR lead, a finance person (for payroll), and sometimes the CEO. Getting everyone on a call takes weeks. You'll send a lot of "just checking in" emails.

The Honest Reality

What's Hard

• Switching costs are real: You're asking companies to migrate employee data, payroll info, and active job postings. Even if they hate their current tools, migration friction kills deals.
• Category is crowded: Rippling has 100x your resources and brand recognition. You'll hear "why not just use Rippling?" constantly. Your answer needs to be crisp.
• Early-stage risk: Some prospects won't buy because you're 15 people. They worry about product roadmap, stability, and support. This objection doesn't go away until you're 100+ people.
• Self-sourcing is a grind: Without SDRs, you're doing prospecting, demoing, and closing. That means less time with warm pipeline and more time on cold outreach that mostly goes unanswered.
• Long cycles with multi-threading: Even mid-market deals take 2-3 months because you need HR, Finance, and sometimes Legal involved. Deals slip quarters often.

What Success Looks Like

• Closing 1-2 deals per month at $20-40K ACV
• Building a pipeline of 15-20 active opps at various stages
• Converting 15-20% of discovery calls to closed-won (industry standard is 10-25%)
• Getting good at handling "you're too small/unproven" objections without getting defensive

Who You're Selling To

Primary Buyers:

• Head of People / VP People at 30-150 person startups (main champion)
• CFO / Finance lead (payroll buyer, cares about cost and compliance)
• CEO / COO at smaller companies (<50 people)

What They Care About:

• Reducing tool sprawl and admin overhead (they're drowning in logins and manual work)
• Compliance confidence (especially multi-state payroll and recruiting compliance)
• Speed of implementation (they need this done before next funding round or big hiring push)
• Cost vs current stack (you're replacing 3 tools—does the math work?)
• Risk of switching (what breaks during migration? what's your uptime SLA?)

Requirements

• 2-4 years selling B2B SaaS, ideally in HR tech, payroll, or recruiting tools
• Comfortable with full-cycle sales—you won't have SDR support initially
• Experience selling into HR/People teams and navigating multi-stakeholder deals
• Ability to explain technical product (integrations, compliance, data migration) without being technical yourself
• Comfortable at an early-stage company—you'll build processes, not follow a playbook
• Self-motivated for outbound—you need to hit activity metrics without a manager breathing down your neck