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Toronto, Ontario, Canada
Onsite
Clio is the global leader in legal AI technology, empowering legal professionals and law firms of every size to work smarter, faster, and more securely.
We are transforming the legal experience for all by bettering the lives of legal professionals while increasing access to justice.
This role is open to candidates across North America (US and Canada, excluding Quebec). If you are located near one of our hubs (Burnaby, Calgary, or Toronto), you will be expected to work in the office a minimum of twice per week on our designated Anchor Days.
Clio is looking for a Director of Product-Led Growth & Billing Systems, a rare, high-impact opportunity to own two of the most strategically important and interconnected areas of our product organization under one mandate for the first time.
This is not a role for someone who wants to inherit a playbook. It's for someone who wants to write one, defend it, and drive it forward in a fast-moving, high-stakes environment.
On one side, you will lead our PLG function across Clio's full and growing product portfolio, building the teams, and growth loops that make the product itself a primary driver of acquisition, activation, and expansion.
On the other side, you will own Clio's Billing System (CBS), our internal system that powers how we configure, quote, package, and ultimately charge our customers. CBS is mission-critical. It sits at the intersection of product, sales, finance, and go-to-market, and nearly every team at Clio has a stake in it. This means priorities shift frequently, every stakeholder has an opinion, and someone needs to hold the line. That someone is you.
The reason these two mandates live together is intentional. CBS is one of the biggest unlock mechanisms for PLG at Clio. Owning both means you have the autonomy to move fast, remove your own blockers, and build growth experiences that aren't constrained by a system you don't control. It also means you need to be exceptionally good at making decisions under pressure and bringing stakeholders along even when they don't get what they want.
Clio has been a sales-led organization for most of its history and that motion has worked. Now our product portfolio has grown to the point where the product itself can and should be a key driver of growth, and our billing infrastructure needs to keep pace with that ambition (amongst others).
We need someone who has lived and led through a PLG transition before. Not just read about it, actually done it. Someone who has felt the friction of installing PLG into a sales-first culture, who has made mistakes and learned from them, and who knows exactly what it takes to make this kind of shift stick.
We also need someone who understands that owning a complex, high-dependency system like CBS is as much about stakeholder management and prioritization discipline as it is about product craft. CBS attracts strong opinions from every corner of the business and priorities are always competing. Your job is to be a fair, clear, and decisive decision-maker across all of them.
Product-Led Growth
PLG strategy and vision across Clio's full product suite, defining the framework, the metrics, and the roadmap for how we grow through the product
Team leadership across multiple squads focused on acquisition, activation, onboarding, and expansion
The growth loop, owning the end-to-end funnel from first touch through activation and expansion, and identifying the highest-leverage places to invest
Experimentation culture, building a pragmatic, fast-moving test-and-learn engine that the whole organization can rally around
AI-enabled growth, actively identifying and deploying AI tools and capabilities to accelerate your team's output and Clio's growth experiments
Clio's Billing System (CBS)
Full product ownership of CBS, Clio's internal system used to configure pricing, generate quotes, manage packaging, and charge customers
Leadership of an existing product team of 2 Senior PMs today, one embedded in PLG and one in CBS, with 3 additional open roles to fill, and full accountability for the roadmap, health, and evolution of both areas
Stakeholder management across a complex, high-demand landscape. Sales, Finance, Marketing, GTM, and Product all depend on CBS, and you will be the person who sets priorities, communicates tradeoffs clearly, and holds the line when needed
Monetization partnership, working closely with the GTM Monetization team as a key stakeholder to ensure CBS enables Clio's pricing and packaging strategy
Decision-making under pressure. CBS is a system where everyone has opinions and priorities shift constantly. You will need to form a clear point of view, advocate for it confidently across senior stakeholders, and make calls that don't always make everyone happy
Across Both
Cross-functional alignment, working shoulder-to-shoulder with Sales, Marketing, Customer Success, Finance, and Data teams to ensure PLG and CBS work in lockstep with Clio's broader go-to-market motion
Executive partnership, reporting into the VP of Product and contributing to how Clio thinks about growth and monetization infrastructure at the portfolio level
Tooling and instrumentation, ensuring we have the data, telemetry, and tooling in place to make confident decisions fast
You have taken a B2B SaaS company from sales-led to product-led, or built significant PLG capability inside an organization that didn't have it. You've got scar tissue from the hard parts and wins you're proud of. You understand that PLG isn't just a top-of-funnel tactic, it's a company-wide operating philosophy, and you know how to initiate and bring people along on that journey.
You are an exceptionally strong stakeholder manager. You've operated in environments where many teams have competing claims on your roadmap and limited patience for hearing no. You know how to listen, synthesize, prioritize, and communicate decisions in a way that maintains trust even when you can't give everyone what they want. You don't avoid conflict, you navigate it well.
You are decisive. You form opinions based on evidence and context, you articulate them clearly, and you stand behind them. You don't need consensus to move forward but you know how to build it when it matters.
You are hands-on. You don't just set direction and manage up. You're in the weeds with your team, reviewing experiments, pushing on tradeoffs, and doing real work alongside the people you lead.
You have a technical enough background to own a complex billing or commerce system. You need to understand the architecture, ask the right questions, and make sound product decisions about a system that has significant downstream consequences across the business.
You've integrated AI into how you work, running experiments, synthesizing data, moving faster. This isn't aspirational for you, it's already how you operate, and you're excited to build a team culture where that's the norm.
10+ years of experience in product growth or product management in a B2B SaaS environment
Demonstrated experience building and scaling PLG across a multi-product portfolio
Experience leading and developing high-performing, cross-functional product teams
Deep fluency in growth metrics: activation rates, time-to-value, expansion revenue, NRR, PQLs, and the systems used to track them
Experience working at or transitioning a sales-led organization toward a product-led model
A technical background sufficient to own and make decisions about a complex product system with broad business dependencies
Proven ability to manage a high-volume, high-stakes stakeholder environment. You've prioritized under pressure, communicated tradeoffs clearly, and held the line on a roadmap
Strong data and analytical skills. You are comfortable owning a metrics framework, running analysis, and building the case for investment based on evidence
Excellent communicator and cross-functional partner. You've influenced without full authority and brought skeptics along
Based in the US or Canada
Experience owning a billing, pricing, or commerce system in a SaaS environment
Experience in legal tech or other regulated-industry verticals
Background that spans both product and marketing. You've sat in both seats or closely adjacent ones
Experience at a company that has gone through a significant growth inflection, Series D and beyond, or post-IPO
What you will find here:
Compensation is one of the main components of Clio’s Total Rewards Program. We have developed a series of programs and processes to ensure we are creating fair and competitive pay practices that form the foundation of our human and high-performing culture.
Some highlights of our Total Rewards program include:
Competitive, equitable salary with top-tier health benefits, dental, and vision insurance
Hybrid work environment, with expectation for local Clions (Vancouver, Calgary, Toronto, Dublin and Sydney) to be in office minimum twice per week.
$2000 annual counseling benefit
RRSP matching and RESP contribution
Clioversary recognition program with special acknowledgement at 3, 5, 7, and 10 years
In addition, this role is eligible for variable pay that is based on company performance, with actual payout amounts calculated and paid on a quarterly basis.
*Our salary bands are designed to reflect the range of skills and experience needed for the position and to allow room for growth at Clio. For experienced individuals, we typically hire at or around the midpoint of the band. The top portion of the salary band is reserved for employees who demonstrate sustained high performance and impact at Clio. Those who are new to the role may join below the midpoint and develop their skills over time. The final offer amount for this role will be dependent on geographical region, applicable experience, and skillset of the candidate.
Diversity, Inclusion, Belonging and Equity (DIBE) & Accessibility
Our team shows up as their authentic selves, and are united by our mission. We are dedicated to diversity, equity and inclusion. We pride ourselves in building and fostering an environment where our teams feel included, valued, and enabled to do the best work of their careers, wherever they choose to log in from. We believe that different perspectives, skills, backgrounds, and experiences result in higher-performing teams and better innovation. We are committed to equal employment and we encourage candidates from all backgrounds to apply.
Clio provides accessibility accommodations during the recruitment process. Should you require any accommodation, please let us know and we will work with you to meet your needs.
Learn more about our culture at clio.com/careers
We're a Human and High Performing AI company, meaning we use artificial intelligence to improve all of our operations. In recruitment, AI helps us streamline the process for greater efficiency. However, we've built our systems to ensure that a human always reviews AI-generated output, and we never make automated hiring decisions.
Disclaimer: We only communicate with candidates through official @clio.com email addresses.