VP People Operations

Toronto, Ontario /
Human Resource/People /
Full time
Drop is a rewards platform on a mission to inspire people to live their optimal lives by empowering them financially. Through our personalized platform, Drop intelligently surfaces the right brands, at the right time, to make members’ everyday better than it was before. Powered by machine learning, Drop matches consumers with over 500+ partner brands to satisfy two main goals: to earn points from their purchases and redeem them for instant rewards.

Headquartered in Toronto, with an office in New York, Drop is backed by world-class investors including NEA, HOF, Royal Bank of Canada, Sierra Ventures, and White Star Capital. 

To learn more, visit: www.joindrop.com, or follow us at @joindrop on Instagram and Twitter.

People Operations at Drop:

Reporting into the CEO, this newly created position echoes Drop’s commitment to developing our most valuable asset, our people. Our People Ops team has been small and robust for 3+ years, scaling and learning alongside the company and we are now looking for a senior leader to bring their experience and guide Drop as we scale beyond Series C. 

What kind of challenges will the VP People Operations be working on at Drop?

    • Develop and support People & Culture initiatives related to: talent acquisition, organizational development, recognition, change management, succession planning, workplace culture, compensation & benefits, HR compliance and employee relations. Involves continually assessing the competitiveness of all programs and practices against relevant comparables.
    • Coach executives and be an effective Business Partner to advise on people strategies and build out practices and programs to attract, accelerate and retain top talent
    • Lead adoption of a product-driven and high-performance culture (incentives, structure, ownership, key messaging etc)
    • Lead our People & Culture team. Empower and leverage the strengths of People & Culture team members to meet or exceed departmental objectives.
    • Develop programs that drive employee engagement and retention, learning and development, and employee relations to create an environment for people to do their best work
    • Initiate and champion opportunities to further diversity, equity and inclusion across the organization
    • Assist managers in recruitment efforts by developing recruiting best practices and strategies that can be rolled out to support hiring efforts across the organizations

What you bring to the table

    • Minimum of 7-10 years of progressive HR and people leadership experience in a high-growth environment with a CHRP designation strongly preferred.
    • In-depth experience relating to: talent acquisition, leadership assessment & organizational development, compensation & benefits, HR compliance & standard practices, and employee relations.
    • Demonstrated ability to work in partnership with CEO and leadership team to provide overall company leadership and direction, as well as working with all levels of an organization.
    • Reputation as a strong communicator, facilitator and coach to manage high performing teams
    • Resourceful, self-motivated with a collaborative team mindset, and ability to work in fast paced changing environments
    • Strong analytical and problem-solving skills; ability to assess situations and make decisions based on data while drawing from previous experience
    • Sets an example for the team of a great attitude and strong value system
    • A self-starter who has the ability to operate at both the strategic level and the tactical execution level
    • Strong knowledge of employment laws, regulations and practices in both Canada and in the USA

Bonus points if

    • Business or talent background within the tech startup industry.
    • Demonstrated experience in organizational development and change management; Previous experience with HR transformation is highly desired.
    • Previous experience communicating with Board Series B+


    • Lifestyle Spending Accounts and Health Spending Accounts + drug, dental, travel, and group insurance coverage
    • Unlimited time off
    • Parental leave benefits
    • Stock options

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At Drop, we're committed to providing an enjoyable and meaningful environment for every member of our team. We operate under a flat structure with minimal hierarchy where everyone’s opinion is valued equally. We are looking for team members with an entrepreneurial mindset who will thrive in a fast-paced and rewarding environment.

Drop Technologies, Inc. is proud to be a diverse and equal opportunity employer and as such does not discriminate on the basis of race, colour, religion, sex, national origins, age, sexual orientation, disability or any other characteristic protected by applicable laws. Selection decisions are solely based on job-related factors.