Technical Support jobs in Winnipeg, MB

Tech Lead

Department: Client Fulfillment / Technical Operations

Location: In Office

Schedule: 9:00 AM – 5:00 PM CDT, Monday to Friday

Reports to: Sr. Client Success Manager (Fulfillment Manager)

About GetTruckDrivers.com

GetTruckDrivers.com helps trucking companies hire CDL drivers faster through the Driver Recruitment Secrets program, our Driver Deploy recruiting software, and done-for-you Meta ad campaigns. Every client launch runs on a stack of Meta Business Suite, ad campaigns, ManyChat chatbots, landing pages, pixels, and Driver Deploy automations that the Tech team builds, supports, and improves.

The role

You own the technical health of every client account and the team that keeps it healthy. You are the final technical escalation point for Client Success Managers and clients, the manager of the Tech Associates, the owner of our technical support system, and the person who turns recurring client problems into product and feature improvements in Driver Deploy and our automations. When a campaign stops delivering, leads stop flowing, or a client is frustrated with their tech, you step in, take ownership, and drive it to a documented resolution.

What you will doClient technical escalations and client handling

• Act as the named owner for every technical escalation: gather full context, set a next-update deadline, coordinate stakeholders, and post updates at each meaningful change until closed.
• Join client calls directly when an issue is blocking delivery, creating churn risk, or affecting a campaign, and communicate what we know, what we are doing, and when the next update will come.
• Partner with CSMs on at-risk accounts and align internal notes with client-facing updates so the client never hears two stories.
• Close every escalation with a root cause, a final resolution, and a preventative action or SOP update.

Solving client problems

• Diagnose and fix the hardest issues across the full funnel: Meta ad delivery and pixel tracking, ManyChat flows and external requests, Driver Deploy automations, A2P 10DLC and domain setup, landing pages, and third-party software (TMS, applications, email clients).
• Spot patterns that repeat across accounts and eliminate them at the source instead of fixing them one client at a time.
• Audit live campaigns and setups for quality, and step in when a setup is wrong before the client feels it.

Managing the technical team

• Lead, coach, and hold accountable a team of Tech Associates against their scorecard KPIs: response time, bug resolution time, QA accuracy, setup completion, and CRM hygiene.
• Run daily tech check-ins and the weekly technical meeting, hold 1:1s, and review end-of-day reports.
• Assign and balance client setups, pre-launch sessions, tasks, and project work across the team, and approve new associates’ first setups and campaigns.
• Onboard and train new technical hires using our SOPs and scorecards, and keep both current.

Managing the technical support system

• Own the technical support workflow end to end: intake from clients and CSMs, triage, prioritization, assignment, tracking, and closure in Notion and Driver Deploy.
• Define and enforce response and resolution standards, and report support volume, resolution times, and recurring issue categories to leadership weekly.
• Maintain and expand our technical SOPs, checklists, and troubleshooting appendices so the team can resolve known issues without you.

Product and feature development and support

• Translate recurring client problems and support tickets into clear feature requests, bug reports, and acceptance criteria for Driver Deploy and our automation stack.
• Build, test, and roll out new automations, AI agents, chatbot templates, and integrations, and QA every release before it reaches clients.
• Coordinate with the CSM, Sales, and Marketing teams on technical requirements for new products and campaign types.
• Document every new feature or process change and train the team and CSMs on it.

What we are looking for

• Experience in technical support for a software or marketing-services company, with some supervisory and project-leading experience.
• A track record of owning client escalations personally and turning frustrated clients into references.
• Deep hands-on expertise with Meta Ads Manager and Business Suite, HighLevel (GoHighLevel), chatbot platforms (ManyChat preferred), API and webhook integrations, and DNS, domain, and email deliverability setup.
• Experience running a ticket-based or queue-based support system and reporting on its metrics.
• Experience scoping and shipping product features or automations with developers, or building them yourself.
• Calm, structured, and direct communicator in writing and on client calls, in clear English.
• Bias for documentation: if it is not in the SOP, you write it.
• Fully responsive on Slack, email, Zoom, and CRM.

How success is measured

Escalation first response - Under 2 hours during business hours

Escalation resolution or mitigation - Under 48 business hours, with a next-update deadline set on every open item

Team bug resolution time - Under 48 business hours across the team

Team QA accuracy - 95%+ error-free deliverables

Technical setup completion - 90% within required timelines

Client satisfaction (tech) - 90%+

Repeat issues - Every closed escalation has a documented preventative action

Team scorecard reviews and 1:1s - Weekly, 100%

Compensation and perks

• Total compensation of $70,000 to $100,000+ per year, made up of three parts:
• A flat monthly salary.
• Technical client fulfillment payouts, earned directly and through your team.
• Client retention bonuses for keeping our clients our clients.
• Paid conferences, training, and courses, plus non-fiction and technical book reimbursement.
• 2 weeks paid vacation plus "My Days" after 1 year

How to apply

Send your resume and a short note describing a client escalation you owned end to end: what broke, how you handled the client, how you fixed it, and what you changed so it never happened again.

angelica@gettruckdrivers.com

Job Type: Full-time

Pay: $70,000.00-$100,000.00 per year

Benefits:

• Casual dress
• Company events
• Dental care
• Extended health care
• Life insurance
• Paid time off
• Profit sharing
• Vision care

Application question(s):

• Describe a client escalation you owned end to end: what broke, how you handled the client, how you fixed it, and what you changed so it never happened again.

Work Location: In person