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Serv Recruitment

Business Leader

Kelowna, BC, Canada

Job type: Full-time
Apply by: Oct 29, 2026
Posting language: English
Posted: Sep 29, 2026

Apply About employer

Applications open in a new tab.

Original job description

Serv, a global executive recruitment partner, is hiring on behalf of our client Martell Group for a Business Leader to run Winly.

Join the Team:

The Martell Group exists to build people, brands, and ventures that create meaningful impact. 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.

Our goal is to attract world-class talent and align people where their impact is greatest. When you apply to Martell Group, you'll automatically be considered for all open roles across our companies, not just the one you applied for.

For more information, visit: https://www.danmartell.com/

Why you shouldn't work here: Radical Transparency from our CEO

About Winly:

Winly 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.

Position Responsibilities:

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.

This role includes:

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.
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.
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.
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.

Qualifications

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.

Our Ideal Teammate Is Someone Who:

Is proactive and accountable
Thinks strategically while remaining highly execution focused
Communicates with clarity and confidence
Thrives in a fast-paced, high-growth environment
Operates with a high level of ownership and accountability
Is comfortable making disciplined tradeoffs and hard decisions
Stays close to customers, the team, and the numbers
Balances strategic leadership with a player-coach mentality
Uses data to drive decisions and continuous improvement
Cares deeply about building enterprise value and measurable business impact

Location: Kelowna, BC (In-Office)

Compensation: OTE $250K to $1M+ (salary, performance-based, and equity compensation)

Serv uses AI tools in our recruitment process, including developing job postings and note-taking during interviews. AI is not used to screen, assess, or select candidates. All resumes are reviewed by a human, and all hiring decisions are made by humans. Any AI-generated output used during the recruitment process is reviewed by a human before action is taken.

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More about this job

Responsibilities

Own Winly’s P&L, growth strategy, sales, customer success, and team, while partnering with the Technical Leader to set product priorities and deliver improvements. Improve acquisition, activation, retention, and enterprise value, and report performance and plans to the board.

Requirements

Candidates should have scaled a sales-led SaaS or subscription business from a few million dollars to $10M+ and/or through an exit, with strong knowledge of unit economics and product management. They should be experienced in leading small teams, making hiring and performance decisions, working directly with customers, and preparing a business for an exit.

Skills

P&L Management
Go-to-Market Strategy
Sales Leadership
Customer Success
Product Management
Product Roadmapping
SaaS Growth
Retention Management
Unit Economics
Financial Forecasting
Pricing and Packaging
Team Leadership
Customer Research
Board Reporting
Mergers and Acquisitions Readiness
Data-Driven Decision-Making

Visa sponsorship

Not detected in the job text

Keywords

Winly
Martell Ventures
AI-Powered CRM
Instagram
Direct Message Sales
Sales-Led SaaS
Subscription Business
P&L
Go-to-Market
Paid Advertising
Sales Funnel
Customer Success
Product Roadmap
Activation
Retention
MRR
NRR
CAC
Gross Margin
Cohort Analysis
Unit Economics
CAC Payback
ARR
Board Reporting
Exit Readiness
Enterprise Value
Martech
Social Selling
CRM

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