Customer Success & Implementation Manager

This position is based full time in Downtown Toronto or Long Island City NY, with a minimum of 3 days in the office per week.
Full time
Toronto / NYC

Apply Today!

Trestle is growing and we can't wait to have you be a part of the team!
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Join us in revolutionizing how the world is built!

At Trestle, we're solving problems that have been entrenched at the intersection of communication and data connectivity in the construction industry for decades. We’re on a mission to improve collaboration and streamline workflows, so projects can be done faster and more cost efficiently.

We work hard, are mission driven, and love rising to a challenge. If you are looking to be part of a fast paced environment with lots of growth and want to build something that literally transforms how the world is built, come on down to Trestleland!

The Role

You’ll be Trestle’s first dedicated Customer Success hire and own the full customer journey from signed contract through long-term retention. You will take full ownership of our customer base, and make sure every customer is live, adopted, and seeing measurable value within their first 90 days.

This role has two distinct components that must both be strong:

  • Implementation: You own getting customers live. That means configuring accounts, managing data migrations, structuring onboarding plans, and driving adoption until the product is embedded in their workflow.
  • Engineering Bridge: You are the primary connector between customers and our engineering team. When a customer has a product request, a bug, or a custom build need, you translate that into clear, prioritized, actionable specs. You don’t just pass tickets, you own the feedback loop end-to-end.

This is an individual contributor role that will eventually build a team. You will be THE customer success function, setting the playbook, running implementation end-to-end, managing renewals, and ensuring the product team always has a clear picture of what customers need.

Responsibilities

Implementation & Onboarding

  • Own the full implementation process for every new customer — from signed contract through go-live and active adoption.
  • Design and maintain a repeatable implementation playbook that gets GCs live and using the product within 30 days.
  • Manage data migrations, account configuration, vendor list setup, and any custom workflow setup required at launch.
  • Deliver product walkthroughs and training sessions adapted to each customer’s technical comfort level.
  • Define and track activation milestones: first login, first vendor submission, first compliance review completed.

Engineering Bridge & Product Feedback

  • Serve as the primary liaison between customers and the engineering team for product requests, bug reports, and custom build needs.
  • Translate customer asks into clearly scoped, prioritized tickets — not just vague requests, but structured specs with context on impact and urgency.
  • Own the feedback loop: communicate back to customers on timelines, set expectations, and close the loop when work ships.
  • Triage incoming requests to distinguish what’s a configuration fix, what’s a standard feature request, and what needs a custom build discussion.
  • Join product planning conversations to advocate for customer priorities and ensure roadmap decisions reflect real field usage.
  • Build and maintain a living document of customer-driven product insights that the team can reference when making prioritization calls.

Retention & Expansion

  • Own the health of our current customer base: Shaw, Posillico, M.B. Kahn, Paul Davis, and growing.
  • Proactively identify customers at risk and act before churn happens — don’t wait for the renewal conversation.
  • Run quarterly business reviews that demonstrate clear ROI and surface expansion opportunities.
  • Identify expansion opportunities (additional offices, divisions, use cases) and collaborate with sales to close them.
  • Manage renewals and work with the CEO on contract structures for growing accounts.

Playbook & Systems

  • Build and own the CS function from scratch — processes, templates, metrics, and tooling.
  • Define success metrics for implementation, activation, retention, and NPS.
  • Set up and maintain customer records, health scores, renewal tracking, and open request status in our CRM.
  • Create reusable implementation materials, training guides, and support documentation.

Requirements

  • 2–5 years of customer success, implementation, or technical account management experience at a B2B SaaS company.
  • Experience in construction technology, field services, or a similarly hands-on, operational industry — this is a strong differentiator.
  • You’ve done real implementation work: configuring software, managing data migrations, setting up accounts, and driving adoption — not just relationship management.
  • You have a track record of being the go-between for customers and product/engineering teams. You know how to turn a customer complaint into a ticket and a ticket into a shipped feature.
  • Ability to understand technical product concepts well enough to scope requests and set realistic expectations — you don’t need to be an engineer, but you can’t be afraid of the product.
  • Track record of managing the full customer lifecycle: implementation, activation, health monitoring, QBRs, and renewals.
  • Excellent communicator who can earn the trust of a GC superintendent in the field and a VP of Operations in the boardroom.
  • Comfortable with ambiguity and energized by building something from scratch.

Preferred Qualifications

  • Prior experience at a construction tech company (Procore, Autodesk Construction Cloud, Levelset, Bridgit, or similar).
  • Familiarity with vendor management, prequalification, or compliance workflows in construction.
  • Experience managing a customer base of 5–50 accounts at a seed or Series A company.
  • Enough technical fluency to read a basic API doc, understand a webhook, or troubleshoot a data import without needing an engineer on the call.
  • Experience with structured product feedback processes — you’ve written specs, user stories, or requirements docs before.
  • Ability to speak credibly about construction workflows — bonus if you’ve worked on a job site or with GCs directly.

What Success Looks Like

At 1 Week

  • You’ve done a full product walkthrough and can navigate every feature without hand-holding.
  • You’ve reviewed every active customer account and know who is healthy, who is at risk, and who has open product requests.
  • You’ve shadowed at least one customer call and one engineering planning session.

At 1 Month

  • You own every active customer relationship. The CEO has stepped back from day-to-day CS and implementation communications.
  • You’ve taken over the open product request backlog from customers and triaged it with the engineering team.
  • You’ve delivered an implementation session or QBR independently.
  • You’ve drafted a v1 implementation playbook and begun systematizing what was previously ad hoc.

At 3 Months and Beyond

  • Zero surprise churn. Every renewal is visible weeks in advance.
  • Customer health scores are tracked and accurate. You know where each account stands without digging.
  • Engineering has a clear, maintained backlog of customer-driven requests with context and priority attached.
  • You’ve shipped at least one product improvement that came directly from a customer conversation you translated into a spec.
  • NPS is measurable and moving in the right direction.
  • You’re actively identifying expansion opportunities within existing accounts and working with sales to close them.

What We Offer

  • Competitive salary commensurate with experience.
  • Comprehensive medical, vision, and dental health plans.
  • Competitive equity options — you’re building this alongside us.
  • Flexible vacation policy.
  • Direct access to the CEO and founding team. Your work will be visible and impactful from day one.
  • A dynamic work environment where you’re building something real, not managing PowerPoint decks.

Apply Today!

Trestle is growing and we can't wait to have you be a part of the team!
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