Head of Sales

Venn Software Inc

$120K — $180K *
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 4+ years of B2B sales experience, with 2+ years in a leadership role
  • Demonstrated success in achieving revenue targets in a fast-paced environment
  • Strong understanding of SMB sales cycles
  • Proven ability to recruit and develop sales talent
  • Data-driven with experience in managing sales pipeline and forecasting
  • Excellent communication skills for building relationships with prospects
  • Familiarity with CRM systems like HubSpot

Responsibilities

  • Own the complete outbound sales strategy and execution
  • Build and manage a high-performing sales team focused on pipeline generation
  • Define and refine Ideal Customer Profiles and account strategies
  • Develop sales playbooks and qualification frameworks
  • Collaborate with other departments on pricing and onboarding strategies
  • Analyze sales data and drive accurate forecasting using CRM tools

Benefits

  • Generous equity ownership tying personal success to company growth
  • Comprehensive medical, dental, and vision insurance
  • Chance to influence the future of business banking in Canada
Full Job Description
About Venn

Venn is transforming business banking for Canadian entrepreneurs. As the ONLY digital banking platform in Canada offering a truly modern solution, we disrupt traditional banking practices. Tired of the big banks' monopoly, Canadian business owners are seeking innovative alternatives.

We've raised $21.5m Series A from Tier 1 investors, and we're rapidly growing and looking to hire A-players to change the future of banking in Canada.

What You'll Be Doing
  • Own Venn's full outbound sales funnel from strategy to execution
  • Build, lead, and coach a high-performing sales team (BDRs and AEs) with a focus on pipeline generation and deal conversion
  • Define and continuously refine our Ideal Customer Profiles (ICPs) and territory/account strategies
  • Develop and implement sales playbooks, cadences, and qualification frameworks
  • Collaborate with product and customer success to shape pricing, packaging, onboarding, and expansion strategies
  • Analyze sales data, monitor KPIs, and drive forecast accuracy using HubSpot (or equivalent CRM)


What we're looking for:
  • 4+ years of B2B sales experience, including 2+ years leading sales teams (startup or scale-up experience preferred)
  • Proven track record of hitting and exceeding revenue targets in a fast-paced environment
  • Deep understanding of SMB sales cycles
  • Ability to hire, onboard, and develop top sales talent
  • Data-driven mindset with strong experience in pipeline management, forecasting, and conversion optimization
  • Strong communicator who can craft compelling narratives and build trust with prospects and partners
  • Comfortable working cross-functionally with marketing, product, and operations
  • Experience with CRM systems (e.g. HubSpot) and sales enablement tools


Bonus Points
  • Experience at an early-stage or fast-growing startup
  • Experience at a fintech


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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