About Actual

At Actual, we’re reshaping the hospitality industry through automation, transparency, and operational efficiency.

Our flagship product, Tip Management, streamlines tip management for businesses and employees, moving hundreds of millions of dollars in tips from employers to employees. We’re expanding into a broader suite of tools to help operators run leaner, smarter, and more profitably.

Backed by N49P, Northside Ventures, Union Capital and other notable investors, we’re a fast-growing startup looking for a Staff Engineer to help scale our platform, improve our architecture, and contribute to new product development

Responsibilities

  • Own the full customer relationship post-sale: onboarding, activation, training, support, and identifying upsell opportunities

  • Manage a portfolio of enterprise and multi-location hospitality operators across Canada and the U.S.

  • Lead complex client onboardings, including custom configuration, integrations (POS, payroll, scheduling), and change management across all units

  • Deliver onboarding sessions and advanced product training tailored to high-value customer needs

  • Build relationships with senior and cross-functional stakeholders to ensure buy-in and long-term alignment

  • Identify and execute on expansion opportunities across new locations, features, and service lines

  • Proactively manage account health and retention through regular check-ins, QBRs, and success planning

  • Use HubSpot and internal tools to track key milestones, usage, and risk signals

  • Collaborate closely with Sales, Product  and Technical teams to improve handoffs, escalate blockers, and inform onboarding priorities

  • Mentor junior Account Managers through coaching, process reviews, and day-to-day support

  • Contribute to onboarding documentation, playbooks, and internal enablement as we scale our approach

What You’ll Bring

  • 3–7 years of experience in Account Management, Customer Success, or Implementation in a B2B SaaS or Fintech company

  • Proven track record managing complex integrated platform implementations and cultivating long-term relationships with enterprise and multi-location clients.

  • Strong project management skills -> you thrive in cross-functional, fast-paced environments

  • Ability to lead and influence senior stakeholders with confidence and clarity

  • Familiarity with HubSpot or similar CRM tools

  • Excel/Google Sheets proficiency. Particularly with multi-site reporting or hospitality metrics

  • Ability to train and develop junior team members to strengthen overall team performance

  • Track record of optimizing onboarding processes and building scalable account management systems

  • Bonus: background in hospitality operations or experience working with restaurant and hotel operators

B2B SaaS & Market Experience

  • Experience supporting customers in a fast-paced, high-growth SaaS environment

  • Ability to manage onboarding and retention across complex organizations with multiple departments

  • Strong understanding of hospitality workflows: especially tip management, scheduling, and payroll

  • Comfortable working across time zones and adapting to client needs at scale

Nice to haves

  • Direct experience supporting enterprise hospitality brands or technology platforms

  • Knowledge of compliance and operational challenges in restaurant or hotel chains

  • Interest in training and developing junior team members

  • Enthusiastic about optimizing onboarding strategy and building scalable systems

Why join us?

  • Be a key part of a fast-scaling company changing the way hospitality teams operate

  • Take ownership of relationships with some of the most well-known operators in North America

  • Help shape the onboarding strategy and client success motion as we grow

  • Collaborate with a mission-driven, supportive team that values accountability and autonomy

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