Enterprise Sales Manager

Fello; Northern (KY); Hybrid; USD 180,000 - 260,000; Full time

Benefits offered by this job

Competitive compensation

Fully remote work

Flexible hours

Equity options

Career growth and development

Paid time off

Job summary

Fello is seeking a seasoned Sales Leader to guide an Enterprise Account Executive team toward larger, multi-stakeholder deals in a fully remote environment. You will shape strategies, review pipelines, and drive forecast rigor while coaching reps in discovery, negotiation, and complex selling motions.

You will lead with hands-on coaching, partnering across Marketing, Product, and Customer Success to align on enterprise deal strategy, compensation, and growth opportunities.

Qualifications

• 5+ years of sales leadership experience with a quota-carrying team.
• 5+ years of software sales experience with deals $50K+ in value.
• Proven success coaching teams through long, complex sales cycles.
• Strong pipeline management and forecasting discipline.
• Hands-on coaching style, in-deals participation and reviews.
• Excellent communication and executive presence to guide tenured reps.

Responsibilities

• Lead and coach a team of Enterprise Account Executives, driving the shift to larger, more complex deals.
• Run regular pipeline reviews, deal strategy sessions, and forecasting cadences for a disciplined enterprise pipeline.
• Coach reps 1:1 and in the field, joining calls and sharpening discovery and negotiation skills.
• Partner with sales leadership to build playbooks, processes, and enabling skills for enterprise deals.
• Develop compensation, quota, and territory structures appropriate for a mature enterprise motion.
• Identify skill gaps and implement targeted coaching plans and enablement to close them.
• Collaborate with Marketing, Product, and Customer Success to align on strategy and customer needs.
• Report on team performance, pipeline health, and deal progression to leadership.

Skills

Sales leadership

Quota bearing

Pipeline management

Forecasting

Coaching

Executive presence

Real estate experience (nice to have)

Job description

Fello is a profitable, hyper-growth, VC-backed B2B SaaS company building the agentic real estate platform of the future.

Our platform combines data intelligence, marketing automation, and conversational AI to help real estate teams engage smarter and scale faster. At the center of it is Felix, our AI teammate, which takes real work off a team's plate — running follow-up across calls, texts, and emails today, with more of the team's day-to-day work coming next.

We're not another tool in the stack. We're the system that powers it — learning, adapting, and executing in real time so teams can focus on growth, not guesswork.

If you're excited about building an AI product that's changing how an entire industry works, you'll fit right in.

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
• 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.