B2B Outbound Sales Associate at CompCrafter

Toronto, Ontario, Canada -

Full Time

Start Date

Immediate

Expiry Date

27 Apr, 26

Salary

0.0

Posted On

27 Jan, 26

Experience

2 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Outbound Sales, Lead Generation, Cold Calling, Cold Emailing, LinkedIn Outreach, CRM Proficiency, Research Skills, Pitching, Metrics Tracking, Feedback Collection, Collaboration, Sales Strategy, Entrepreneurial Mindset, Relationship Building, HR Tech Knowledge, SaaS Experience

Industry

Software Development

Description

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 leads Build and maintain a strong pipeline of HR leaders, founders, and operations executives at startups, SMBs, and mid-market companies Conduct discovery calls, deliver short pitches, and book demos for the founder Test messaging, hooks, and angles to increase reply and meeting-booking rates Track metrics (open rates, call outcomes, meetings booked, conversion to opportunities) Provide frontline feedback on objections, buyer hesitations, pricing perceptions, and product expectations Collaborate closely with the founder to refine ICP, value props, and sales motion Help build the outbound playbook that future sales hires will follow Fluent English 2+ years of experience in outbound-heavy B2B sales, SDR/BDR, or business development roles Proven history of crushing outreach targets and consistently booking meetings High-volume cold outreach experience Strong research skills and ability to personalize outreach at scale Confident delivering quick pitches to senior HR and business leaders Proficient in a CRM and sales engagement tool is an asset Highly independent, proactive, and motivated by results You 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 team Are energized by outbound prospecting and building relationships from scratch Have 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 benefits Uncapped 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 strategy Autonomy & flexibility: Fully remote, outcome-driven role where you set your approach A path to leadership: Future opportunities in sales leadership, growth, or partnerships as we scale

Responsibilities

The B2B Outbound Sales Associate will be responsible for generating pipelines and driving top-of-funnel momentum through high-volume outbound outreach. This includes conducting discovery calls, delivering pitches, and booking demos for the founder.