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Director of Sales

Sales Contract Remote

About the role

The current sales motion is founder-led and almost entirely inbound. It works — but it won't scale. We need someone to build the outbound muscle, write the playbook, and hire the team that runs it. You'll start by closing deals yourself, learning the objections and what moves buyers, then build the process around what you learn. Our ICP is clear — SMB warehouse operators and distributors who've outgrown spreadsheets or are overpaying for bloated ERPs — the product is genuinely useful, and it's free to start. At six months, the benchmark is a repeatable outbound motion, a live HubSpot pipeline the founders can trust, and at least one AE ramping to quota.

What you'll do

  • Build the outbound motion from scratch: define ICP tiers, prospecting sequences, and territory model before you hire the first rep
  • Negotiate and close mid-market deals yourself while the team is small — this is a player-coach role with a quota attached
  • Own pipeline metrics end-to-end: coverage ratio, stage conversion, average sales cycle, and forecast accuracy; report to the CEO weekly on what's off
  • Stand up HubSpot (or equivalent) as the system of record — deal stages, forecasting, activity tracking, and win/loss reasons from day one
  • Hire, onboard, and ramp the first 2–3 account executives; write the playbook and call-coaching rubric they'll run
  • Work with marketing and product to tighten the funnel: improve trial-to-paid conversion and shorten time-to-first-value
  • Feed competitive and market intelligence back to the founders weekly: objections you're hitting, which competitors come up, which features close or lose deals

What we're looking for

  • 6+ years in B2B SaaS sales, including at least one stint as a first sales hire or early sales leader at a company building its motion from scratch
  • You've built or substantially scaled a sales process — you know what it means to have no SDR support, no established brand, and limited inbound volume
  • Data-driven: you can walk through your pipeline coverage, ramp curve math, and quota assumptions on a whiteboard without preparation
  • Excellent coach and closer — you can work a deal yourself and teach someone else to replicate it

Nice to have

  • Experience selling inventory, ERP, operations, or logistics software to SMBs
  • Familiarity with the wholesale, distribution, or 3PL world — you understand who the buyer is and what they care about
  • A track record as a first or second sales hire at a company that actually scaled

Apply for this role

Send us your résumé and a short note about why this role. We read every application.

Apply by email

or email [email protected]

About Count My Boxes

Inventory software thousands of small businesses run on. Part of Pangloss Technologies.

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