Head of Sales

Wise Pelican is hiring a Head of Sales who will own our new revenue number and carry a quota alongside the team that hits it. This is a player-coach role: you lead Sales reps, you sell every day, and you are commissioned on both your individual quota and the team's. Every lead you touch is already warm. They are real estate agents who have signed up or built a profile inside Wise Pelican, and your job is to turn them into paying clients and grow the ones who already pay. You will work closely with our Customer Success team, who own post-purchase support, so you can stay focused on conversion and expansion.

Wise Pelican is an innovative leader in real estate marketing solutions, empowering real estate professionals with cutting-edge tools and services. As a growing company with a global workforce, we foster a dynamic, inclusive work environment that promotes growth, innovation, and collaboration. We are on a three-year path to $20 million in annual revenue, and this role is one of the biggest levers for getting there.

This position is a full-time, onsite role based in Scottsdale, Arizona. 

• Carry your own quota and sell alongside your reps every day: convert free and profile-only users into paying subscribers, and upgrade existing clients to higher plans and add-ons.
• Lead and manage a small team of Sales reps, set clear expectations, and drive accountability toward monthly new-revenue and expansion goals.
• Audit our current commission structure and propose what should change to align with company financial goals. 
• Build and own the dashboards for pipeline health, forecast accuracy, free-to-paid conversion, one-time to subscription revenue, upgrade rate, and rep attainment. Partner with RevOps on lead scoring, routing rules, and SLAs.
• Drive growth by shortening speed-to-value for new signups, building handoff playbooks from in-app signals to Sales, and tightening free-to-paid conversion through nudges, lifecycle campaigns, and ROI-driven CTAs.
• Coach, mentor, and develop your reps using AI call reviews to produce coaching snippets, talk-track upgrades, and sequence tweaks.
• Partner with leadership on forecasting models, scalable processes, and clean data (sequence compliance, source attribution, persona tags) so reps work from views that help them sell.
• Collaborate with Marketing, Product, and Customer Success so Sales strategy lines up with campaigns, product features, and the post-purchase experience.

At first…

• Learn the product, ramp on your own quota, and start closing within your first 30 days.
• Audit the current commission plan and present a recommendation to the CEO within your first 90 days: what stays, what changes, and why.
• Evaluate the small Sales function and identify quick wins and fix processes that are broken.
• Establish a consistent coaching rhythm and the handful of performance metrics that move the number.
• Define the handoff between Sales and Customer Success so buying signals get to you and post-purchase issues get to them.

Once you get your footing…

• Set pipeline coverage targets and quarterly pipeline creation goals by source (new signups, profile-only users, existing-client expansion).
• Report on the Sales KPIs that matter most to the business: attainment, free-to-paid.

• 5+ years of progressive Sales experience with at least 2 years leading a team, preferably in SaaS or subscription B2B.
• A closer who still loves to sell. You have carried an individual quota while managing others and hit both.
• A skilled coach with a track record of developing reps into consistent performers.
• Fluent in pipeline management, forecasting, and data-driven decision making.
• Comfortable leading an inbound, product-led motion where leads are warm and the job is conversion and expansion, not cold prospecting.

• You have been the player-coach before: carried your own number, led a small team, and grew both at the same time.
• You use AI tools and vibe coding in your daily work: building your own dashboards, scripts, call-review workflows, or small internal tools instead of filing a ticket.
• You have built Sales practices from scratch and are not afraid to test and experiment with new ways of hitting a revenue goal.

• Major Medical Insurance: Working at Wise Pelican gives you endorphins. Endorphins make you happy. And happy people just don't get sick. But…if that does happen, we offer Major Medical Insurance to assist with life's biggest nuisance.
• Dental & Vision Coverage: An eye for an eye. A tooth for a tooth. Talking dental and vision insurance, of course. No need for revenge when eyes and teeth are insured.
• Paid Time Away: The PTA you want to be involved with. Employees are given 3 weeks of Paid Time Off. Also Sick Time. Also Parental Leave. Also 7 Company Holidays per year.
• Professional Development Stipends: "Pay me what you owe me! Don't act like you forgot! WPBHMM!" – You to Wise Pelican about fronting the bill on your professional development needs.
• 401(k) at tenure milestone: We hope you'll want to stop working here one day. This should help.
• Compensation: This role is benchmarked to the Scottsdale market and carries a base salary of $100,000-$125,000 per year. It is also commissioned on both your individual quota and your team's quota, with total on-target earnings of $180,000 to $207,000. Offered compensation is based on merit and relevant qualifications.