The Role
Own enterprise client and prospect relationships, lead consultative product demos, support deal closing, and serve as a workforce and HR subject-matter expert. The role develops go-to-market strategies for specialty retail, partners with marketing on positioning, translates customer and market feedback into product opportunities, and advises Product on roadmap priorities, compliance, integrations, and hourly workforce needs.
Summary Generated by Built In
About Shiftlab:
Shiftlab is a fast-growing, AI-driven workforce management platform. Over 30,000 retail professionals already rely on us for scheduling, time and attendance, team communication, and real-time performance visibility — the everyday tools that make running an hourly workforce simpler for operators and better for the people on the floor.
We're a fully remote company built on trust, ownership, and collaboration. Our mission is to elevate human potential, and for us that starts on the frontline: less time lost to manual scheduling and paperwork, more visibility and control for the people actually running the stores.
About The Role:
This is a strategic, client- and prospect-facing role. We're looking for someone who can own Enterprise client relationships and help close deals. You'll sit with sales and marketing as a credible expert voice in the room with prospects, lead demos for enterprise accounts, and give Product a seat-at-the-table view of what enterprise HR buyers actually need.
**This is a remote opportunity. Our preferred locations are: Regina, Vancouver, Toronto, Denver, Davidson/Charlotte
The #1 filter for this role (note for HR)
Above everything else, we're looking for a closer — someone you can put in a boardroom with a prospect and trust to help win the deal. Domain depth matters here because it wins deals, not for its own sake.
What You'll Do:
Sales engineering & deal closing
What You Bring:
What We Offer:
Want to Join the Team?
If you’re interested in a career with ShiftLab, please submit your resume and cover letter. We are an equal opportunity employer. We do not discriminate based on race, faith, colour, cultural background, gender, sexual orientation, age, marital status, or disability status. We thank all applicants for their interest, however, only those selected for an interview will be contacted.
You can view our job applicant privacy policy here.
Shiftlab is a fast-growing, AI-driven workforce management platform. Over 30,000 retail professionals already rely on us for scheduling, time and attendance, team communication, and real-time performance visibility — the everyday tools that make running an hourly workforce simpler for operators and better for the people on the floor.
We're a fully remote company built on trust, ownership, and collaboration. Our mission is to elevate human potential, and for us that starts on the frontline: less time lost to manual scheduling and paperwork, more visibility and control for the people actually running the stores.
About The Role:
This is a strategic, client- and prospect-facing role. We're looking for someone who can own Enterprise client relationships and help close deals. You'll sit with sales and marketing as a credible expert voice in the room with prospects, lead demos for enterprise accounts, and give Product a seat-at-the-table view of what enterprise HR buyers actually need.
**This is a remote opportunity. Our preferred locations are: Regina, Vancouver, Toronto, Denver, Davidson/Charlotte
The #1 filter for this role (note for HR)
Above everything else, we're looking for a closer — someone you can put in a boardroom with a prospect and trust to help win the deal. Domain depth matters here because it wins deals, not for its own sake.
What You'll Do:
Sales engineering & deal closing
- Sit directly with sales as a credible expert voice in the room — this is a lead role in prospect and client conversations, not a back-seat supporting one
- Lead product demos for enterprise prospects, tailoring each pitch to that vertical's specific
- Help build and run a go-to-market strategy for specialty retail
- Partner with marketing on positioning, messaging, and collateral for new target verticals
- Bring the human side of the conversation — speak credibly to the real operational and people impact HR/workforce systems have on both the business and its frontline staff
- Speak knowledgeably to the compliance complexity around hourly workforce management — labor law, scheduling regulations, wage/hour rules — as it comes up in prospect conversations
- Translate the nuance of third-party integrations — payroll systems, internal operating systems, POS systems — well enough to speak credibly to a prospect's requirements and connect the dots for our internal teams
- Act as our in-house expert on HR and hourly-workforce issues in retail — bring that lens into prospect and customer conversations
- Gather and synthesize feedback from prospects, customers, and industry contacts to spot unmet needs before they show up in a support ticket
- Product voice
- Hold a seat at the table on product roadmap decisions
- Help ensure the product both innovates and checks the compliance/operational boxes enterprise HR buyers require
- Work with Product to turn market and customer signals into concrete opportunity briefs — not just “customers want X,” but why, and what it's worth
- Identify HR and workforce management pain points specific to hourly, multi-location workforces and help Product prioritize what we build next
What You Bring:
- A closer, first — proven ability to hold your own in a boardroom with a prospect and help win the deal; this is the top filter for this role, ahead of raw domain tenure
- 10+ years in HR, retail operations, or workforce management — ideally some combination of the three
- Direct experience with hourly, frontline workforce environments at scale (retail, restaurant, or similar multi-location operations)
- Enterprise experience — you've operated inside, or served, large and complex organizations
- Working knowledge of the compliance landscape around hourly workforce management (labor law, scheduling regulations, wage/hour rules)
- Comfortable leading client-facing conversations in a consultative, expert capacity
- Conceptual (not necessarily technical) fluency with third-party integrations — payroll, POS, and internal operating systems — enough to speak credibly to a prospect's requirements and translate for internal teams
- Comfort operating across sales, customer-facing, and product work — this isn't a role for someone who wants a single lane
- Experience giving product demos or leading prospect-facing conversations
- A track record of turning an operational or HR pain point into a clear business case or product requirement
- Strong written and verbal communication — you'll be translating between sales, CS, and product regularly
- Self-starter who's comfortable building a go-to-market motion in a new vertical largely from scratch
- Hands-on technical aptitude with integrations or systems — a genuine asset if you have it, but not something we screen for
- Experience in specialty retail categories beyond telecom — apparel, jewelry, beauty, or other regulated or hourly-heavy retail
- Background with HRIS, payroll, or workforce management software
- Prior experience at an early-stage SaaS company
What We Offer:
- Begin your journey with a competitive starting salary!
- Compensation: The expected base salary range for this role is $130,000–$160,000 CAD, plus variable compensation. The overall compensation package will reflect the successful candidate’s experience and the final scope of the role.
- Enjoy peace of mind with a comprehensive benefits package for you and your entire family.
- Embrace work-life harmony with a flexible remote working environment, generous vacation and trusted sick leave program.
- Invest in your future with our RRSP/401K/PF and Share Ownership plans. What's even better? We offer a match program!
- We care about your family, offering maternity, adoption, and paternity leave salary top ups as well as ten “New Baby Days” for all parents welcoming a new child into their life.
- Enjoy a “Cultural Day” off annually to celebrate a day of religious or cultural significance.
- Give back with up to 6 days of paid time off annually for volunteering or personal learning.
- We believe in the value of taking time to refresh, re-energize, and reflect on your career journey. Employees are granted a seven-week sabbatical after every seven years of employment!
Want to Join the Team?
If you’re interested in a career with ShiftLab, please submit your resume and cover letter. We are an equal opportunity employer. We do not discriminate based on race, faith, colour, cultural background, gender, sexual orientation, age, marital status, or disability status. We thank all applicants for their interest, however, only those selected for an interview will be contacted.
You can view our job applicant privacy policy here.
Skills Required
- Proven ability to act as a closer, hold credibility in boardroom prospect conversations, and help win deals
- 10+ years of experience in HR, retail operations, workforce management, or a combination of these areas
- Direct experience with hourly, frontline workforces at scale in retail, restaurant, or similar multi-location operations
- Enterprise experience operating inside or serving large, complex organizations
- Working knowledge of labor law, scheduling regulations, wage and hour rules, and hourly workforce compliance
- Experience leading client-facing conversations in a consultative, expert capacity
- Conceptual fluency with payroll, POS, and internal operating system integrations
- Ability to work across sales, customer-facing, and product functions
- Experience giving product demos or leading prospect-facing conversations
- Track record of converting operational or HR pain points into business cases or product requirements
- Strong written and verbal communication skills
- Self-starter able to build a go-to-market motion in a new vertical
- Hands-on technical aptitude with integrations or systems
- Experience in specialty retail categories beyond telecom, such as apparel, jewelry, or beauty
- Background with HRIS, payroll, or workforce management software
- Prior experience at an early-stage SaaS company
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The Company
What We Do
About Chrysalis Chrysalis is a meta-company operating in the SaaS space, with the mission to create technology that elevates the human experience. We do this by nurturing the companies that grow organically within the Chrysalis ecosystem, and by acquiring like-minded businesses that complement our mission. Chrysalis, its teams, and its companies develop software solutions that enable people to create memorable and valuable moments where the digital meets the personal. We embrace a vision of a world in which people bring their whole selves to whatever they do and engage creatively and constructively to the benefit of all. Current companies within the Chrysalis ecosystem include: iQmetrix, North America’s leading provider of retail management solutions for the telecom sector; Ready, an award-winning contactless menu and payment app for the hospitality and events industries; Cova, North America’s leading provider of retail management solutions for the cannabis vertical; and Shiftlab, a scalable, performance-based, AI-driven workforce scheduling platform designed for retail organizations. Chrysalis is a privately held company headquartered in Vancouver, British Columbia, with four additional offices across North America.
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