Jobs in Toronto, Canada

Company: 021 Strategic
Department: Operation
Reports to: Managing Partner
Location: Remote-first (preference for Canadian time zones)

021 Strategic helps innovative startups and scaleups access and optimize non-dilutive funding, specializing in SR&ED, government grants, and funding strategy. We provide white-glove, hassle-free service while leveraging technology to scale our impact. Our mission is to unlock funding that accelerates innovation. We are growing fast, with a high-performance, ownership-driven culture.

This is our first dedicated Customer Success hire, stepping into a function previously held by our sales team. As our founding Customer Success Manager, you will play a critical role in shaping how we support and grow our client base—building scalable systems, defining playbooks, and setting the standard for high-touch, proactive client care.

You’ll work closely with our leadership and service teams to ensure a seamless post-sale experience for our clients—most of whom are CEOs, technical founders, or CFOs managing complex and deadline-driven funding initiatives.

This role is ideal for someone who’s worked at a fast-growing company or scale-up and has helped build CS systems from scratch while thriving in environments that require both strategy and hands-on execution.

• Own the client journey post-sale—onboarding, engagement, and retention
  
  
• Set clear expectations, build trust quickly, and become a strategic partner to each client
  
  
• Proactively identify risks and prevent churn through timely check-ins and milestone management
  
  

• Build the CS function from the ground up—establish SOPs, workflows, reporting tools, and automation to support long-term scale
  
  
• Collaborate with leadership to co-design the client lifecycle, NPS loops, and referral programs
  
  

• Track key client milestones (e.g., SR&ED submissions, grant deadlines) to ensure timely and accurate delivery
  
  
• Serve as the connective tissue between clients and our internal teams (e.g., technical writers, funding analysts)
  
  
• Use tools like HubSpot, Notion, and Google Workspace to manage performance and visibility across accounts
  
  

• Identify opportunities for upsell, cross-sell, and referrals based on client needs and lifecycle stage
  
  
• Provide feedback loops to the sales, marketing, and product teams to improve the customer experience
  
  

• You’ve been the first CS hire or worked in an early-stage environment where you helped build the playbook
  
  
• You’ve worked at a fast-growing startup or scale-up, and you know what it takes to build structure amid growth
  
  
• You are energized by solving operational chaos and turning ad hoc processes into repeatable systems
  
  
• You’re equally comfortable speaking with CEOs and wrangling spreadsheets
  
  
• You thrive in fast-paced, ambiguous environments and love owning outcomes
  
  
• You’re a natural communicator who can simplify complex ideas for non-technical audiences

• 3–5 years in Customer Success, Account Management, Consulting, or similar client-facing roles
  
  
• Experience at a fast-growing company or scale-up is required
  
  
• Prior experience building or refining CS workflows and playbooks
  
  
• Experience with startups/scaleups or B2B service environments
  
  
• Familiarity with HubSpot, Notion, and Google Workspace

• Exposure to government funding programs like SR&ED, IRAP, or CanExport
  
  
• Background in financial, technical, or grant-related consulting

• You embody extreme ownership, a core value at 021 Strategic. You don’t pass the buck—you solve the problem.
  
  
• You operate with integrity and put client outcomes above shortcuts or quick wins.
  
  
• You thrive in ambiguous environments, love improving processes, and roll up your sleeves to get things done.
  
  
• You understand what it means to move with urgency without sacrificing quality.
  
  

• Client NPS / satisfaction score
  
  
• Client retention & renewal rate
  
  
• Onboarding time-to-complete
  
  
• Milestone completion rates

• $120k–$150k OTE (base + commission) with no cap—a top performer will exceed $200k.
  
  
• Equity/profit-share potential as we scale.
  
  
• Remote-first flexibility with a Toronto hub for events.
  
  
• Vacation, wellness days, and professional-development budget.
  
  
• Plenty of runway for career growth as we scale—shape it your way.
  
  

If you’re excited about building the customer success function from scratch at a fast-growing, impact-driven company, we want to hear from you. Apply here and email us your proudest CS systems-build or a short note about your client success philosophy to careers @ 021strategic. com. Bonus points if you attach something that shows how you think.