Customer Success Manager (CSM)

Teamwork.com is an agentic PSA (professional services automation) platform that helps businesses win, plan and deliver projects more profitably. We connect projects, resourcing and financials in one place, so leaders get real numbers from real delivery, not guesswork, and can price work on purpose, deliver it for less, and grow margin over time. Our tagline puts it plainly: most tools track work, we make it profitable.

Project management tools can't manage money, so run delivery through one and you lose margin without ever seeing where. Finance-first tools capture the numbers, but delivery teams resist using them, so the data going in is bad and the numbers coming out are worse. Teamwork.com is built to do both: resourcing, financials and margin visibility captured as delivery happens, not bolted on afterwards, in a platform teams actually want to use.

We believe in hiring great people and look to ensure everyone has the best possible experience of work, every day. We strive to be open and transparent, humble and customer focused. And we thrive on curiosity, getting results and working together relentlessly to deliver excellence. We are a company of action, full of triers and doers: we try things, we make mistakes, and we learn from them.

We pride ourselves on doing right by our customers, working with brilliant people, and going above and beyond. Our personality is unmistakable: we work hard, take joy in our wins and each other's successes and important life events. And we care and support each other when life throws lemons. More than anything we embrace a straightforward approach to getting things done. We are fanatical about our customers, and when talent meets passion, success happens.

This is a remote role but you must reside in Ontario with the right to work in Canada

About Teamwork

The opportunity

As a Customer Success Manager, you will own a named book of professional-services customers and act as their primary point of contact throughout their lifecycle with Teamwork.com. You are accountable for adoption, value realisation, renewals, and expansion identification, and your performance is measured against Gross Dollar Retention (GDR) and Net Dollar Retention (NDR). You also own the renewal commercially, leading the conversation, negotiating terms, and carrying the number.

Your customers are professional-services businesses whose profitability depends on billable hours, utilisation, and project margin. Your role is to make sure Teamwork.com is helping them deliver client work more efficiently and more profitably. Features are the vehicle, not the destination. Our north star is the value customers realise through better business outcomes, and your job is to make that value clear and tangible well before they reach a renewal.

This is a proactive, relationship-led role. You run onboarding from start to finish, working alongside Professional Services on data migration and technical setup, and then carry the relationship through adoption and renewal. You work closely with Support, Sales, and Product to give customers a consistent experience and to flag risks and opportunities early. You keep a clear view of upcoming renewals, customer health, and the value delivered. You own renewal preparedness and risk identification, and you work with Sales to progress the expansion signals you spot.

This role is ideal for a commercially confident CSM who is ready to own a book of business, lead their own renewals, and take full accountability for retention outcomes within a scaling Customer Success organisation.

How We Work: AI-First

AI is part of how this team works every day. We use it to take the manual effort out of account management, which frees up time for the customer conversations that drive retention. We expect you to be comfortable using AI in your daily workflow and to apply your own judgement to everything it produces. The people who do best on this team tend to go a step further and build their own tools/agents and workflows.

Responsibilities Include:

• Portfolio Ownership: Proactively manage a dedicated book, driving deep product adoption, health, and retention across the entire customer lifecycle.
• Executive Business Reviews (EBRs): Move past the tactical features. You will lead regular strategic reviews with agency leadership to demonstrate ROI, visualize utilization data, and align Teamwork.com with their bottom-line profitability goals.
• Expansion & Commercial Health: Partner closely with Account Executives and Renewals managers to spot growth signals, mitigate churn risks early, and unlock expansion revenue within your patch.
• Workflow Architecture: Act as an expert on agency operations. You'll map their specific business processes to Teamwork.com's advanced capabilities (resource management, budgeting, and time tracking).
• Voice of the Customer: Code and document client feedback, feature requests, and operational friction points to advocate for your portfolio directly with our Product and Engineering teams.
• Playbook Innovation: Help build the scale-up machine. You will contribute to internal customer success playbooks, health-scoring models, and retention strategies to optimize our team's performance.

Requirements

• 3–5 years of experience as a dedicated Customer Success Manager or Account Manager managing a B2B SaaS portfolio (Mid-Market or Enterprise tier preferred).
• This is a remote role. You must be based in Ontario and have the legal right to work in Canada.
• Agency / Professional Services Knowledge: You understand how billable hours, project margins, and utilization rates work. Speaking the language of agency operations is a massive advantage.
• Consultative Communication: Exceptional ability to build trust quickly, navigate complex account politics, and lead value-driven presentations.
• Data-Literal: Comfortable diving into customer health metrics, CRM tools (HubSpot/Salesforce), and CS platforms to build data-backed retention strategies.
• The Underdog Mindset: You are a proactive doer who thrives in a fast-paced environment where you can take action and directly impact company growth.

What good looks like

Customer Adoption & Outcomes

Customers can clearly state the business outcome they bought Teamwork.com to achieve, and they know whether they are getting it. You help customers reach those outcomes by adopting the features and workflows that get them there. Customers reach value in good time, and that value is backed by evidence rather than assumed.

Renewal Readiness & Retention

You keep clear visibility of renewal dates, health, risks, and next steps across your portfolio. You surface churn risk early and work through it with a structured save plan, rather than defaulting to feature pitches or discounts. You lead the renewal commercially, with stakeholders mapped, ROI demonstrated, and terms negotiated. Customers come into a renewal aligned and without surprises, and you deliver directly against the GDR target for your book.

Expansion Identification

You identify expansion through increased usage, additional teams, or broader product adoption. You surface qualified expansion signals to Sales and support them through to close. You contribute to NDR through value-led expansion.

Account Ownership & Communication

You run effective customer cadence, onboarding follow-ups, and adoption reviews. You set clear expectations, communicate progress, and follow through on what you commit to.

Operational Excellence

Customer notes, health signals, renewal context, and next steps are accurate and up to date in our systems, including renewal forecast fields. You use product usage data and customer feedback to decide where to spend your time. You apply the team's playbooks and help improve them where you see a better way.

What you can expect

Core Benefits and Perks

• Employee Share Options (ESOP) — we mean what we say when we say, “act like an owner”!
• Competitive salary & OTE (as applicable)
• Up to 30 days vacation from day 1
• Pension (401K), Dental and Health Insurance benefit 
• Give Back and Mentoring program
• Wellbeing programs
• Educational resources and generous allowance to support development
• Inclusive policies - maternity, paternity & parent leave, as well as a focus on flexible working 
• Recognition programs

Teamwork is an Equal Opportunity Employer, and qualified applicants will receive consideration for employment without regard to race, colour, religion, sex, sexual orientation, gender identity, or national origin.

We may use AI-assisted tools to help our recruitment team review and assess applications against the criteria for a role. These tools support our recruitment team and do not make automated hiring decisions. Applications and hiring decisions remain subject to human review.