Director of Sales, ContactMonkey

• Living in Toronto (GTA) and can commute to our Downtown Toronto office 3x a week
• 8-10 years of experience in B2B software sales - ideally both high velocity as well as enterprise selling success
• 5 years of people leadership experience in B2B sales with at least 1 year managing managers
• You’ve successfully driven net-new business growth across North America through a proactive, outbound sales strategy targeting mid-market and enterprise accounts
• Experience using LinkedIn as a prospecting, lead generation, and communication tool
• Expertise using SaaS tools, such as Salesforce, Salesloft, Gong, Clay, Nooks
• Experience embracing AI to drive efficiencies in the sales process and scaling sales teams

Desirable

• Join the Sales team, where you’ll have the opportunity to win net new business and be at the forefront of business growth
• Our Director of Sales isn’t just closing deals—you're a strategic hunter, driving enterprise growth and building a predictable, scalable revenue engine
• In this role, you’ll report to the VP of Sales and work towards 50% YoY growth alongside the Sales and Marketing, who strive for excellence every day
• Leading BDR and AE teams, who are smart, ambitious, and ready to grow
• Your job is to set the bar, keep motivation high, coach them to be their best, and make sure everyone is clear on goals and expectations
• Performance that drives results: you’ll own the key metrics—response times, conversion rates, pipeline impact, quota achievement—and make sure the team is not just tracking to them, but beating them
• When something’s off, you’ll spot it fast and get things back on track
• Scaling that works: we’re building for 50% YoY growth, so processes need to be clean, efficient, and repeatable
• You’ll bring structure without slowing us down—making smart use of tools like Salesforce, Gong, LinkedIn, Salesloft, Clay, Nooks), to keep the team running smoothly and transparently
• Always testing, always improving: you’ll lead with curiosity—constantly experimenting with what messaging, cadences, and workflows actually move the needle
• Work closely with marketing to run tests, learn quickly, and double down on what works
• Sales enablement: You’ll make sure the team is set up to win—designing onboarding tailored to inbound sales, coaching on real call scenarios, and running regular training sessions that sharpen skills to help us move up market to the enterprise space
• This means refining qualification criteria for complex buying groups; coaching reps on multi-threading and enterprise messaging; and aligning closely with marketing and sales leadership to prioritize and route high-value accounts effectively
• You'll also team up with marketing to keep reps equipped with the right content at the right time, and use frontline insights to keep improving tools and training