Job Title: VP Operations & Business Execution

Location: Remote

Type: Equity-based leadership role (early-stage)

About Pocketride Pocketride is an AI-powered rideshare platform built for underserved cities, focused on safety, reliability, and dismantling the rideshare gray market. With 3,500+ riders and 200+ drivers already on our waitlist, we are preparing for launch and scaling our operations with solid leadership

Position Overview We are looking for a VP Operations & Business Execution to take full ownership of how Pocketride runs day-to-day as we move into launch and scale. This is not a coordination or support role.This role owns execution, reliability, and operational readiness across the company.You will work closely with the CEO,CTO and functional VPs (Tech, Marketing & Growth, Finance, HR & Admin) to ensure strategy turns into reality.

What You’ll Own Customer Success & Trust Operations

Build and own customer support and escalation workflows

Oversee Trust & Safety operational processes

Ensure consistent, high-quality customer experience

Track and improve customer experience metrics (NPS, CSAT, resolution time)

Driver Operations

Own driver onboarding execution and readiness workflows

Manage driver lifecycle operations and communications

Ensure operational reliability of supply at launch and beyond

Insurance & Risk Execution

Own incident documentation and claims-trigger workflows

Work closely with Finance (who owns insurance decisions and costs)

Partner, Investor & Stakeholder Operations

Own operational onboarding of partners

Ensure delivery on partnership commitments

Maintain execution credibility with investors and stakeholders

Legal & IP Program Management Coordinate with external legal counsel on: contracts, IP filings (patents, trademarks) and regulatory matters

Track legal and IP timelines, deadlines, and documentation





Ensure nothing legal or IP-related slips through the cracks

(Note: legal authority remains with external counsel)

HubSpot & Customer Operations

Own the operational use of HubSpot as the company’s central customer and stakeholder management platform

Build and maintain workflows for rider, driver, partner, and stakeholder lifecycle management

Establish CRM processes for lead capture, onboarding, follow-ups, escalations, and customer support

Ensure accurate and consistent customer and operational data across HubSpot

Develop dashboards and reporting to track customer activity, onboarding progress, support cases, conversion, retention, and operational performance

Work with Marketing & Growth to ensure seamless handoffs between marketing, sales, onboarding, and operations

Identify opportunities to automate repetitive operational workflows and improve response and resolution times

Own HubSpot process governance, ensuring teams follow defined workflows, data standards, and operational protocols

Internal Operations & Scale Readiness

Build SOPs and cross-team handoffs

Own launch readiness checklists and operational dashboards

Ensure teams are execution-aligned and unblock issues early

What This Role Does NOT Own

Product roadmap or engineering decisions (Tech)

Brand strategy or growth campaigns (Marketing & Growth)

Insurance selection or financial exposure (Finance)

Hiring strategy, L&D;, or people compliance (HR)

Legal interpretation or final legal decisions (External Counsel)

Who You Are

A strong operator with startup or marketplace experience

Systems-oriented, decisive, and calm under pressure

Founder-level mindset with real ownership mentality

Excited by early-stage ambiguity and building from zero

Why Join Pocketride

Equal-equity leadership role

Direct impact on launch and scale

Work alongside experienced functional VPs

Build operations for a company solving real safety and access problems

📌 VP Operations (Winnipeg)
🏢 Pocketride
📍 Winnipeg