Director, Sales

About Venn Venn is the fastest-growing B2B fintech in Canada. We're on a mission to transform business banking for Canadian entrepreneurs and are looking to hire A-players interested in disrupting traditional banking practices. As the ONLY digital banking platform in Canada offering a truly modern solution, we have seen accelerated growth—scaling to support more than 10,000 Canadian businesses in under two years. Business owners are tired of the big banks' monopoly and are looking for modern tools that replace the legacy systems that have been their only option for over 100 years. We've raised over $26.5M from Tier 1 investors such as Gradient, Left Lane Capital, Intact, and XYZ Venture Capital. Interested in redefining the future of banking in Canada? Look no further. About the Role This is a high-impact leadership role stepping in to lead our sales organization - you’ll continue to build the sales engine, sharpen the fundamentals, and set the team up to compound. You'll report directly to the co-founders and own the day-to-day of how Venn sells. What You'll Be Doing Lead, manage and scale a team of Account Executives and BDRs—setting goals, running 1:1s, coaching to quota, and holding the bar on performance. Own sales enablement end-to-end: onboarding, ramping, ongoing training, playbooks, and the tooling that makes the team faster. Run weekly deal review and forecast calls; pressure-test pipeline, unblock late-stage deals, and make sure nothing slips through the cracks. Build the GTM engine for BDRs—sequencing, cadences, territory design, ICP targeting, and the feedback loops between outbound activity and pipeline quality. Partner with the team on overall GTM strategy, pricing experiments, and the metrics that matter (pipeline coverage, conversion rates, ramp time, win rate, ACV). Work cross-functionally with Marketing, Product, and Ops to make sure sales feedback shapes the roadmap and the demand engine. What You'll Need 6+ years in B2B sales, with 2+ years leading and managing BDRs and/or AEs in a high-growth environment. A track record of hitting (and helping a team hit) quota in a fast-paced startup or scale up. Proven ability to define and execute GTM strategy while building scalable, repeatable motions across segments. Strong sales operating rhythm: forecasting discipline, deal review, pipeline hygiene, and a clear point of view on what great looks like. Coaching instinct. You can listen to a call, watch a demo, or read a deal note and tell someone exactly what to do differently tomorrow. Demonstrated ability to leverage AI to improve sales productivity, pipeline generation, and customer engagement. Experience incorporating AI tools and workflows into prospecting, research, personalization, and deal strategy. Bonus Points Experience at an early-stage or fast-growing startup Experience selling B2B fintech, SMB financial services, or horizontal SaaS Built or scaled an outbound BDR function from Perks & Benefits Healthy equity ownership, among the most generous in the market, aligning your success with the company's growth. Comprehensive coverage of medical, dental, and vision insurance. Opportunity to shape the future of business banking in Canada and beyond.

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