B2B Outbound Sales Associate

2 days ago

Toronto, Canada CompCrafter Full time

This is an early-stage role designed for someone who wants to get in at the ground floor of a fast-growing startup. While the base role is commission-only for the first ten (10) weeks, the time commitment is intentionally flexible (10–15 hours/week), and high performance can quickly lead to a paid, extended, or full-time position with equity opportunities.CompCrafter is an HR tech startup on a mission to help employees understand and maximize the full value of their compensation. We believe total rewards go far beyond salary: health benefits, equity and pension plans deserve just as much clarity and transparency.Beyond awareness, CompCrafter actively encourages smarter, more sustainable use of benefits by guiding employees toward preventive care, proactive planning, and year-round engagement with what their employer already offers. The results are better health outcomes, longer-term financial wellbeing, and benefits that actually get used (not forgotten).We’re early-stage, fast-moving, and passionate about reimagining how people experience compensation. Joining CompCrafter now means stepping in as a founding team member: someone who will help define our sales engine and directly shape the company’s growth trajectory.What You’ll Do This role is pure outbound. You’ll be responsible for generating pipelines, starting conversations, and driving top-of-funnel momentum. You will:Own high-volume outbound outreach across cold calls, cold emails, and LinkedIn to generate qualified leadsBuild and maintain a strong pipeline of HR leaders, founders, and operations executives at startups, SMBs, and mid-market companiesConduct discovery calls, deliver short pitches, and book demos for the founderTest messaging, hooks, and angles to increase reply and meeting-booking ratesTrack metrics (open rates, call outcomes, meetings booked, conversion to opportunities)Provide frontline feedback on objections, buyer hesitations, pricing perceptions, and product expectationsCollaborate closely with the founder to refine ICP, value props, and sales motionHelp build the outbound playbook that future sales hires will followRequirementsFluent English2+ years of experience in outbound-heavy B2B sales, SDR/BDR, or business development rolesProven history of crushing outreach targets and consistently booking meetingsHigh-volume cold outreach experienceStrong research skills and ability to personalize outreach at scaleConfident delivering quick pitches to senior HR and business leadersProficient in a CRM and sales engagement tool is an assetHighly independent, proactive, and motivated by resultsYou Might Be a Good Fit If You…Are entrepreneurial and thrive on ownership: you’re motivated by the opportunity to be an early member of a founding teamAre energized by outbound prospecting and building relationships from scratchHave prior B2B sales, business development, or partnerships experience (SaaS or HR tech a plus, but not required)Are passionate about HR tech, total rewards, and helping employees understand their benefitsBenefitsUncapped commission: Earn more as you close more. Equity opportunity: As an early team member, you’ll have the opportunity to earn equity and grow alongside the company.High-impact experience: Work directly with the founder to shape go-to-market strategyAutonomy & flexibility: Fully remote, outcome-driven role where you set your approachA path to leadership: Future opportunities in sales leadership, growth, or partnerships as we scale

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