About You:You're a sales leader who has built and coached teams selling enterprise deals, and you know what it takes to move a team from transactional selling into complex, multi-stakeholder, longer-cycle deals. You've managed quota-carrying reps before, but more importantly, you know how to develop them - how to coach discovery, deal strategy, forecasting rigor, and pipeline management so a team can consistently close bigger business.
You're a seasoned operator who levels up teams: bigger deals, longer sales cycles, more complex buying committees, and a bigger pipeline to manage along the way. You lead from the front, you're comfortable in deal reviews and live coaching, and you know how to build the muscle memory a team needs to sell at a higher altitude.
You Will:- Lead and coach a team of Enterprise Account Executives, driving the team's shift from smaller, faster transactions into larger, more complex deals with longer sales cycles
- Run regular pipeline reviews, deal strategy sessions, and forecasting cadences that bring discipline and predictability to a growing enterprise pipeline
- Coach reps 1:1 and in the field - joining calls, reviewing deal strategy, and sharpening discovery, negotiation, and multi-stakeholder selling skills
- Partner with sales leadership to build the playbooks, processes, and skills the team needs to consistently win enterprise deals
- Develop and refine compensation, quota, and territory structures appropriate for a maturing enterprise motion
- Identify skill gaps across the team and build targeted coaching plans and enablement to close them
- Collaborate cross-functionally with Marketing, Product, and Customer Success to align on enterprise deal strategy and customer needs
- Report on team performance, pipeline health, and deal progression to sales leadership
You Have:- 5+ years of sales leadership experience, directly managing a quota-carrying sales team
- 5+ years of software sales experience, with a track record of selling and/or leading teams that sell $50K+ deals
- Demonstrated success coaching sales teams through longer, more complex sales cycles and larger deal sizes
- Strong pipeline management and forecasting discipline, with experience instilling that rigor in others
- A hands-on coaching style - you're in the deals with your team, not just reviewing numbers after the fact
- Excellent communication and executive presence, with the credibility to coach tenured reps through a real shift in how they sell
- Real estate industry experience is a plus, but not required - we're looking for depth in sales leadership and bigger-deal selling first
Our Benefits:- Competitive Compensation: Attractive salary and benefits package.
- Flexible Work Environment: Fully remote work with flexible hours to promote work-life balance.
- Professional Growth: Opportunities for career advancement and professional development.
- Health & Wellness: Comprehensive health, dental, and vision insurance plans.
- Paid Time Off: Generous PTO and paid holidays to recharge and relax.
- Collaborative Culture: A supportive team environment that values innovation and collaboration.
- Equity Options: Opportunity to own a part of Fello and share in our success.
- Cutting-Edge Projects: Work on innovative products that leverage AI and advanced technologies.
