About

• Canopy Connect is building the infrastructure that powers best-in-class insurance experiences. We empower consumers to gain value and convenience from their own data, and we enable businesses to securely and quickly support their customers.
• We're growing quickly and are scaling up. As our Head of GTM, you will lead Canopy Connect’s revenue organization. You'll own the complete sales strategy across our diverse customer segments, from high-volume SMB packages to complex enterprise deals and partnerships, while building and scaling a world-class revenue team.
• This is an opportunity to play a pivotal role at an early-stage, well capitalized startup. We've got very strong product market fit in some segments. In other segments we have emerging product market fit. We need a strong Head of GTM to own our revenue number and lead our sales team.
• About you
• Proven experience scaling a B2B SaaS startup from $0-$10m ARR
• At least 3 years of experience managing a mixed sales team of 5+ SDR/BDR/AE including hiring, managing, motivating, coaching, and setting quotas and comp plans
• Instituting repeatable sales processes and CRM hygiene
• Driving pipeline generation, forecasting accuracy, and performance management to exceed revenue targets
• History of closing complex enterprise sales motions
• Experience with low ticket high volume SaaS sales
• Superlative communication skills (verbal and written)
• Bonus: Understanding of insurance, mortgage and auto space
• Sales Strategy
• Create and execute the GTM sales strategy for SMB, Mid-market and Enterprise teams
• Optimize sales processes and methodologies for each customer segment and deal complexity
• Sales Leadership
• Prepare for and participate in quarterly meeting with the board of directors
• Recruit, hire, and manage a mixed sales team of 5+ SDRs, BDRs, and Account Executives
• Create comprehensive sales training and enablement programs to accelerate rep productivity
• Negotiate Canopy Connect’s most complex deals with customers and channel partners
• Implement performance management systems and compensation structures that drive results
• Foster a high-performance sales culture focused on collaboration and continuous improvement
• Revenue Operations
• Collaborate with marketing on lead generation, qualification, and handoff processes
• Partner with customer success on expansion and retention strategies
• Manage sales forecasting, pipeline health, and territory planning
• Strategic Partnerships & Market Development
• Build relationships with key prospects and strategic accounts in insurance, mortgage, and automotive verticals
• Identify channel partners and appropriate GTM motions that protect Canopy Connect’s interests
• Represent the company at major industry events and conferences such as ITC, MBA, NADA, NIADA
• Collaborate with product team on roadmap priorities based on market feedback
• Please note that we are only accepting candidates who are authorized to work in the United States or Canada.
• Our Benefits
• Healthcare: We offer company-sponsored health, dental and vision insurance for employees and dependents.
• Equity: We are a team of owners and we provide our team with generous equity grants.
• Time to Recharge: We offer unlimited paid time off. Unplug, recharge, and come back refreshed.
• Remote Friendly: We are a fully distributed team. We all work remotely. We offer a $1,000 stipend to equip you with a home office that is comfortable and personalized to your needs.
• Friday Reimbursed Lunch: Order lunch on Fridays, and we'll cover it!
• 401K: We offer a 3.5% match.
• Our Core Values
• Be Worthy of Trust | We are building critical infrastructure that processes sensitive data. We earn trust every day by being transparent, honest and clear to all stakeholders.
• Find a Way | We seize opportunities and iterate quickly. We refuse to get blocked. We are relentlessly optimistic about possibilities. Tenacious and creative, we find a way.
• Own It | We are owners of the product and the company, and we own our successes as well as our failures. We value people who embody extreme ownership.
• Think “We” Not “I” | We prioritize the success of the team over individual contributions. The best decisions are made through triangulating the opinions of the team. Productive disagreement leads to good decisions. We don’t tolerate brilliant jerks.
• Raise the Bar | Our standard is to be the best in the world at what we do. We redefine excellence each day.
• To protect the interests of all parties, Canopy Connect will not accept unsolicited resumes from any source other than directly from a candidate. Any unsolicited resumes sent to Canopy Connect will be considered Canopy Connect property. Canopy Connect will not pay a fee for any placement resulting from the receipt of an unsolicited resume. Canopy Connect will consider any candidate for whom an Agency has submitted an unsolicited resume to have been referred by the Agency free of any charges or fees.