Compensation: OTE $250K to $1M+ (salary, performance-based, and equity compensation) Location: Kelowna, BC (In-Office) Across our four companies, we combine audience, operators, and execution to launch scalable products and empower ambitious leaders in Media, B2B SaaS, and AI. Founded by serial entrepreneur and investor Dan Martell (investor in Udemy, Intercom, and Unbounce), we're building a company that values leadership, growth, and simplicity, and we're looking for people who live those values too. Winly is an AI-powered CRM for teams that sell in the DMs.

The AI drafts replies, coaches the rep, and keeps every conversation moving toward a booked call. We'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. Work with the growth team to ensure paid advertising funnels are scaling, and resourced with the right messaging, positioning, offers, funnels and assets.

Iterate on pricing, packaging and positioning to ensure Winly has a clear and compelling position in the market. 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.

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. Build the business, not only the funnel 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’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. Consistently scaling growth with healthy unit economics and CAC payback periods that creates confidence in continued capital investment. Decreasing churn and increasing NRR over time as the result of improvements in onboarding, customer success, product and pricing.

A explicit, 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. The right people in the right seats, including the closer and the Technical Leader, each with a scorecard.

📌 Survey Field Lead (Kelowna)
🏢 Dan Martell
📍 Kelowna