Compensation: OTE $250K to $1M+ (salary, performance-based, and equity compensation)
Location: Kelowna, BC (In-Office)
About WinlyWinly is an AI-powered CRM for teams that sell in the DMs. Coaches, consultants, and course creators run their Instagram sales conversations through Winly. The AI drafts replies, coaches the rep, and keeps every conversation moving toward a booked call. Winly is a Martell Ventures portfolio company.
About the RoleWe're hiring a Business Leader to run Winly.
You'll own the P&L, the team, and the growth engine, with the goal of scaling Winly from a company with strong initial traction and growth, into an exit-ready asset with great product, healthy retention and rapid growth.
You'll lead a lean team across sales, customer success, and engineering, and report to the Martell Ventures partners. You'll also own product strategy and execution: turning customer insight into a focused roadmap, making disciplined tradeoffs, and ensuring the team ships improvements that drive activation, retention, and growth.
What You'll Do1. Own the growth engine- Own the go to market strategy for Winly and work with the growth team to ensure channels, funnels and conversion methods are working and improving over time.
- Work with the growth team to ensure paid advertising funnels are scaling, and resourced with the right messaging, positioning, offers, funnels and assets.
- Set the sales rhythm: booked calls, show rate, close rate, annual mix. Coach the closer directly when it matters.
- Iterate on pricing, packaging and positioning to ensure Winly has a clear and compelling position in the market.
2. Own retention- Ensure customers get activated, stick around, and expand over time.
- Manage the customer success team
- Align sales and customer success to make sure everyone has aligned expectations and incentives.
3. Run the company- Own the P&L, the forecast, and the plan you agree with the board.
- Lead the team across sales, customer success, and engineering. Partner with the Technical Leader to own the product roadmap, prioritize ruthlessly, and translate customer and business needs into clear requirements and measurable outcomes.
- Hire, coach, and make the hard calls on people.
4. Build the business, not only the funnel- Keep the operating metrics clean and current: MRR, NRR, CAC, gross margin, cohorts.
- Report to the board monthly with the clarity of someone who owns the outcome.
What You Bring- You've taken a sales-led SaaS or subscription business from a few million to $10M+ and/or to an exit. You know what healthy unit economics look like across the business, and how to measure them consistently.
- You have strong product management chops. You can synthesize customer feedback and product data, define the highest-leverage problems to solve, write clear requirements, and lead a technical team from discovery through launch and iteration.
- You understand how to prepare a business for an exit event: clean metrics, durable retention, diligence code a team that runs without you.
- You've led a small team through change. You can hire, coach, and part ways with people.
- You're a player-coach. You're not afraid to get your hands dirty, talk to customers, sit on demos, and stay close to the problems in the business.
- Bonus: You're familiar with the space Winly plays in in some way (You've sold to this ideal customer profile, you've built Martech products before, you have experience in social media software, sell by chat/social selling, CRM or other chat based GTM products.
Success Looks Like (First 120 Days)- The plan. A 90 day plan and 12 mo strategy agreed with the board, with monthly targets for key metrics across the company.
- Growth. Consistently scaling growth with healthy unit economics and CAC payback periods that creates confidence in continued capital investment.
- Retention. Decreasing churn and increasing NRR over time as the result of improvements in onboarding, customer success, product and pricing.
- Product. A clear, evidence-based roadmap is in motion based on real feedback from customers, with priorities tied to activation, retention, and growth and a consistent cadence of shipping and learning.
- Team. The right people in the right seats, including the closer and the Technical Leader, each with a scorecard.
- Visibility. Weekly and monthly reporting on key metrics the board trusts.
- Growing Enterprise Value: ARR and the things that affect the multiple that revenue trades are are improving every month, with a clear plan to maximize enterprise value at a liquidity event.
