Jaimie Hackston

Calgary, AB, Canada

Designing the system behind sustainable growth.

I partner with founders and executive teams to architect post sale engines that scale. I bring structure to Sales to Success handoffs, integration strategy, and cross functional delivery so revenue is protected beyond closed won. When operating models are intentional, execution stops relying on heroics and starts compounding.


I work across Success, Product, Engineering, and Operations to turn reactive delivery into durable infrastructure: integrations become strategic levers, handoffs are intenti…

Jaimie Hackston

Experience

  • ZayZoon

    ZayZoon

    Project Manager, Operations (Integrations and Partner Delivery)

    Aug 2022 - Feb 2026

    ZayZoon’s mission is to improve employee financial health and wellness by providing on-demand access to earned wages. By aiming to save 10 million people $10 billion, the company works to eliminate reliance on predatory loans and overdraft fees, offering tools that promote financial flexibility and stability

    • Built and scaled a formal Integrations function, establishing governance, ownership clarity, and cross-functional operating models to support predictable partner delivery.
    • Led complex payroll, T&A, PEO, and embedded integrations, aligning Product, Engineering, Architecture, and Success to accelerate time to value and reduce delivery risk.
    • Directed enterprise CRM and workflow rebuilds, standardizing partner rollout pipelines, stage gates, and reporting to improve onboarding consistency and revenue visibility.
    • Led company-wide transformation initiatives including client journey redesign, revenue optimization and assurance, contract and rev share centralization, and client transition redesign.
    • Owned and led revenue protection and risk mitigation programs focused on the Cross-Functional Risk Escalation Model and year-end loss reduction, enhancing portfolio health and improving margin control.
    • Served as internal consultant on success teams workflow architecture, technical gap analysis, and team maturity frameworks to elevate Partner Success capability.
    • Rebuilt Integrations 2.0 post GTM restructure, redefining ownership models, delivery standards, backlog alignment, and performance metrics to stabilize scale.
  • RecallMax

    RecallMax

    Program Manager, Success Operations and Enablement

    Oct 2020 - Aug 2022

    MaxAssist’s (formerly RecallMax) mission is to streamline dental practice efficiency by transforming time-consuming administrative tasks into simple processes, thereby maximizing productivity and patient care.

    • Owned onboarding and technical support program design, delivery, and scale, driving performance standards, QA frameworks, and operational maturity while leading through influence across Support and Operations.
    • Mentored onboarding leads across implementation planning, workflow design, go-live readiness, and post-launch success, strengthening execution quality and escalation discipline.
    • Served as escalation authority for Level 3 technical issues, partnering with Engineering on data integrity, workflow failures, server mapping, and structured bug prioritization.
    • Rebuilt the client onboarding journey, reducing time to onboarding from six to three weeks and adoption from three months to six weeks.
    • Implemented Salesforce as the onboarding and support source of truth, introducing structured workflows, SLAs, documentation standards, and visibility that reduced rework and improved resolution speed.
    • Increased support throughput from 8 to 22 daily closed tickets per specialist by introducing troubleshooting frameworks, escalation scripts, and CRM-driven standards.
    • Designed and launched an enterprise partner operating model, reclassifying complex multi-location customers and building dedicated onboarding, support, and CSM structures.
    • Established QA reviews, KPI governance, and cross-functional feedback loops linking Support, Sales, and Engineering to drive continuous improvement and product refinement.
  • Absorb Software

    Absorb Software

    Implementation Project Manager

    Apr 2019 - Oct 2019

    Absorb is a cloud-based learning management system (LMS) engineered to inspire learning and fuel business productivity. Our online learning platform combines forward-thinking technology built to scale as your organization grows, with superb customer service rarely seen in the LMS space.

    • Led end to end implementation of Absorb LMS including scoping technical needs, designing integration plans, preparing data migrations, and configuring REST API connections.
    • Managed fifteen or more concurrent onboarding projects and coordinated multi stakeholder timelines while maintaining partner experience quality.
    • Delivered targeted training and enablement to drive adoption and long term satisfaction.
  • Repsol Sport Centre

    Repsol Sport Centre

    Interim Director of Operations & Facility Services (Promoted from Duty Manager)

    Aug 2015 - May 2019

    MNP Community & Sport Centre is a world class sport and fitness facility that inspires individuals and teams to achieve their goals and dreams through innovation, expertise and passion.

    • Promoted into enterprise operations leadership, overseeing three departments and 47 staff across frontline service delivery, facilities, and safety operations within a high-volume, complex environment.
    • Owned end-to-end operational performance including budget accountability, vendor and contract governance, capital planning, workforce planning, and service quality metrics.
    • Designed and implemented standardized operating procedures, escalation frameworks, and risk controls to improve consistency, response time, and cross-team accountability.
    • Led incident management and crisis response programs, establishing structured reporting, compliance documentation, and preventative risk mitigation practices.
    • Rolled out a new CRM as a centralized source of truth, redesigning workflows and data capture processes to improve visibility, reporting accuracy, and performance management.
    • Strengthened onboarding and training programs, improving ramp time, decision clarity, and frontline execution quality.
    • Acted as the operational escalation point across departments, balancing real-time service recovery with long-term systems improvement.
  • REAL ASSIST CONSULTING

    Change Management Consultant (Fractional Advisory)

    Jun 2012 - May 2015

    REAL ASSIST CONSULTING was a boutique operational transformation firm advising real estate brokerages on digital modernization, scalable infrastructure design, and structured change adoption across multi-office teams.

    • Served as a modernization partner to real estate brokerages, leading end-to-end operational transformation from paper-based processes to fully digital, scalable operating models.
    • Architected brokerage-wide workflow redesign across conveyancing, compliance, CRM, and transaction management systems, aligning technology, people, and performance metrics.
    • Advised principals and leadership teams on digital strategy, infrastructure investment, and long-term operational scalability.
    • Directed multi-office change initiatives impacting 50+ staff per engagement, establishing structured onboarding, performance frameworks, and accountability models to drive sustained adoption.
    • Oversaw CRM implementation and system configuration, integrating cross-functional teams while maintaining business continuity during transition.
    • Designed enablement programs empowering realtors to own and manage branded digital presences, strengthening autonomy and client acquisition capabilities.
    • Applied behavioral psychology methodologies to guide leadership through workforce transitions, reduce resistance, and embed durable cultural change.
    • Delivered measurable improvements in process efficiency, reporting accuracy, and team performance through structured change architecture rather than tool deployment alone.
  • SMART Technologies

    Major Accounts Specialist

    Jun 2011 - Jun 2012

    SMART Technologies is a Calgary-based, Foxconn-owned company founded in 1987, renowned for inventing the SMART Board® interactive whiteboard. It develops advanced, AI-powered interactive displays and software designed to improve collaboration in education and business environments. The company specializes in user-friendly touch and ink technology for classrooms and workplaces

    • Managed educational district accounts across the United States, overseeing end-to-end program delivery from funding qualification through implementation, adoption, and renewal.
    • Directed the U.S. School Funding Program, operationalizing a national initiative that enabled underfunded school districts to secure grant funding for SMART Board technology and modernize classroom infrastructure.
    • Designed and managed the funding-to-deployment workflow, aligning Sales, district leadership, procurement, and technical teams to ensure structured handoffs and predictable rollout timelines.
    • Partnered with superintendents, IT directors, and finance stakeholders to translate district goals into scalable implementation plans tied to measurable classroom outcomes.
    • Scoped technical requirements and infrastructure readiness across multi-site districts, mitigating deployment risk and coordinating cross-functional execution.
    • Established repeatable enablement and onboarding frameworks that improved time to adoption and increased long-term program retention.
    • Served as the operational bridge between field Sales, education leadership, and internal delivery teams to ensure revenue realization post-sale and sustained partner growth.
  • WestJet Airlines

    WestJet Airlines

    Inflight Operational Trainer & Talent Partner

    Apr 2002 - Jun 2009

    WestJet is Canada's second-largest airline and a major provider of low-cost, leisure-focused air travel, founded in 1996 and based in Calgary. It operates a fleet of nearly 200 aircraft to over 100 destinations across North America, Central America, the Caribbean, Europe, and Asia. The airline is known for focusing on Western Canada connectivity, with a hub at Calgary International Airport

    • Expanded from frontline operations into recruitment and structured onboarding evaluation, supporting quality assurance and performance readiness during rapid organizational growth.