Senior Sales Representative

• Own net-new pipeline — outbound, inbound, and warm intros from the founder — and run it end to end.
• Run discovery calls with security, compliance, and engineering leaders at regulated 25-to-75-person companies preparing for a first or next audit.
• Deliver product demos against a live Trailbrace workspace; tailor the walkthrough to the buyer’s framework, source stack, and audit window.
• Drive evaluation cycles through connector setup, framework mapping, SOC 2 / ISO / HIPAA readiness milestones, and pilot close.
• Maintain CRM hygiene with a weekly forecast, deal-stage notes, and lost-deal retros that feed product and marketing.
• Partner with the founder on pricing, packaging, and contract structure for the pilot cohort.
• Build the first renewal playbook; own renewals through the first contract year.
• Capture customer objections and patterns; turn recurring themes into product feedback, marketing messaging, and reference customers.
• Represent Trailbrace at security and compliance community events; ship one short-form case study per quarter.
• Hit and document the ramp, ramp curve, and weekly activity baselines that the second sales hire will copy.

• 4+ years closing B2B SaaS deals in the $15K–$150K ACV range; a track record of personally sourced and closed deals, not just team-managed pipeline.
• Demonstrated success selling to a security, compliance, GRC, IT, or engineering buyer — you know what "controls library," "evidence trail," and "audit window" mean in a real conversation.
• Comfortable running full-cycle sales with no SDR layer; you qualify, demo, propose, negotiate, and close.
• Excellent written communication; you write the follow-up email someone actually reads.
• Bias toward async, low-meeting work; you will be one of the first hires and the calendar will be lean by design.
• Authorized to work in the United States.

• Prior experience selling into the regulated-team ICP — SOC 2, ISO 27001, HIPAA, PCI, FedRAMP-adjacent, or audit and attestation services.
• Familiarity with the continuous-evidence / GRC-platform landscape — you have sold against or alongside Vanta, Drata, Secureframe, Sprinto, or Hypersight-class tools, or you have been a buyer of those tools yourself.
• Experience ramping a founder-led sales motion from zero to a repeatable playbook.
• Comfortable presenting to both security practitioners and C-level buyers (CTO, CISO, sometimes CEO).
• Light technical fluency — you can read an IAM policy or a pull-request review policy and know what would survive a SOC 2 spot-check.

• Build the motion from first principles — you will write the playbook the next two hires copy.
• High-trust surface area — you will sit 30 minutes from the CEO on every deal, with real authority on pricing and packaging.
• A buyer that is ready — a regulated team preparing for an audit is closer to 'yes' than most SaaS buyers; the funnel is short and the pain is concrete.
• A product that earns the close — by the time you are in the demo, evidence is already on the trail; you are not selling a deck.
• Compounded commission economics — selling continuous-evidence subscriptions, not one-time attestations, turns each close into a multi-year book.

• Remote-first: work from anywhere in the United States. We default to asynchronous writing; the calendar stays lean by design.
• Competitive base compensation plus meaningful equity — offer specifics tailored to level and location, discussed candidly during the process.
• Medical, dental, and vision coverage; a retirement plan with company match; a stipend for home office and for ongoing learning.
• Paid time off that respects both state requirements and the team’s pace, plus parental leave for primary and secondary caregivers.
• A direct line to the founder; the function you join sits one seat from product, revenue, and engineering on the org chart.

Offer specifics are tailored to level and location; we discuss them candidly during the process. The bullets above are intentionally generic on dollar amounts and counts.

Trailbrace is an equal opportunity employer. We hire on the basis of merit and qualifications, without regard to race, color, religion, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity or expression, age, disability, national origin, citizenship status, marital status, veteran status, genetic information, or any other characteristic protected by federal, state, or local law. We are committed to building a diverse team that reflects the regulated buyers we serve.