Our client, is the premier end-to-end appraisal software solution for the commercial real estate (CRE) industry, used by top valuation and appraisal firms across the United States, Canada, and Australia. As they expand their footprint from midmarket to enterprise-level sales, and explore new opportunities in adjacent spaces, they are seeking a dynamic and experienced Head of Sales to lead their sales team to continued success.
Position Overview:
The Head of Sales will be responsible for driving revenue growth, leading a team of Senior Account Executives (AEs) and a Sales Engineer, and refining the sales strategy as they scale from midmarket to enterprise accounts. You will own the sales playbook, implement strategies to penetrate new verticals, and ensure consistent execution to meet and exceed revenue targets. This role will play a critical part in their go-to-market strategy, particularly with their new data product offering.
You will have a track record of scaling sales teams, managing complex sales cycles, and driving ARR growth in the B2B SaaS space. Your ability to coach a high-performing team, manage long-term deal cycles (3+ months), and close large multi-year contracts will be key to your success. This position requires a blend of strategic leadership and tactical execution to build on our momentum and guide them into new markets.
Key Responsibilities:
- Sales Leadership: Lead and manage a team of 3 Senior Account Executives (each with a $800k ARR quota) and 1 Sales Engineer, driving consistent achievement of team and individual sales targets.
- Player/Coach: Whilst you will be leading a team you will also be responsible for driving your own leads at a high level and meeting an individual goal to support the revenue growth of the company.
- Sales Strategy & Playbook: Refine, scale, and execute the sales playbook to maintain momentum in the midmarket and enterprise segments while transitioning into new verticals (banking, lenders).
- Pipeline Management: Oversee the entire sales pipeline from lead generation to deal closure. Ensure team maintains healthy pipeline management, driving accountability for each stage of the sales cycle.
- Team Development: Coach and mentor AEs to increase deal velocity, improve win rates, and foster career growth within the sales organization.
- Go-to-Market Expansion: Lead go-to-market efforts for new product offerings, with a focus on data solutions.
- Revenue Growth: Drive revenue from $26k average ARR deal size with 2-3 year contracts, ensuring scalability and alignment with company objectives.
- Market Expansion: Expand their TAM by targeting new enterprise clients in the US, Canada, and Australia, while supporting international growth efforts.
- Cross-functional Collaboration: Work closely with marketing, product, and customer success teams to align sales strategies, refine messaging, and provide feedback to continuously improve offerings.
- Reporting & Analytics: Analyze sales data, track performance metrics, and present results to executive leadership on a regular basis.
Qualifications:
- 2+ years of sales leadership experience, managing teams of Senior Account Executives or similar roles.
- 5+ years of B2B SaaS sales experience, ideally selling to midmarket or enterprise clients.
- Proven track record of meeting or exceeding sales targets, with strong experience in multi-year contract negotiations and complex sales cycles (3+ months).
- Experience selling to commercial real estate (CRE), banking, or other related industries is highly preferred.
- Knowledge of appraisal, valuation, or data-driven solutions for CRE firms, and adjacent sectors.
- Strong leadership and coaching abilities, with a track record of mentoring high-performing sales teams.
- Ability to work cross-functionally with marketing, product, and executive teams to align on strategy and execution.
- Excellent communication, negotiation, and presentation skills.
Why our client?
- Be part of a fast-growing, innovative company that is shaping the future of commercial real estate technology.
- Opportunity to lead a team in a high-impact role with autonomy to shape the sales strategy and directly influence the company’s growth trajectory.
- Competitive compensation, equity options, and benefits.
- Join a collaborative, passionate team that values creativity, growth, and success.
