let’s build the future of work together

Chief Technology Officer (CTO)

We’re growing! We Are Rosie is hiring a Chief Technology Officer.

  • We typically include a salary range on our postings, but this is our (very first ever) CTO. This role will be a critical piece on our leadership team and we cannot wait to see *all* the different CTOs and future CTOs that are interested in building the future of work with us. For that reason, our comp is flexible so we can partner with someone who lights us up and is lit up by our mission. 
  • Cool perks! A yearly stipend for professional and personal development, 25 PTO days per year, and an opportunity to join a truly incredible team at a company that is building the future of marketing. 
  • This position can work from anywhere in the US and will report directly to our CEO.


The Company   

We Are Rosie (the “Company”) is building the future of marketing with a thriving community of thousands of independent marketing experts. We Are Rosie is dedicated to creating a better way to work for everyone. The company launched in 2018 with the mission to support extraordinary independent marketers, while providing a way of work that treats everyone with dignity and access to opportunity. Our community of 10,000+ “Rosies” makes it possible for forward-thinking brands and ad agencies to leverage flexible talent and embrace remote/flexible work as inclusion. We are working every day to thoughtfully disrupt the agency, consulting, and staffing models of marketing services.

Despite only being four years old, We Are Rosie currently works with 20+ Fortune 500 brands, the big six holding agency companies, and indy agencies. The Company is growing in excess of 100% / year and has been featured in Business InsiderCampaign US, and AdWeek. In addition, our founder has been awarded Visionary/Founder of the Year (2020) by AdAge, and was named in AdWeek’s 2020 Creative 100 List. We Are Rosie finished near the top of Adweek’s latest Fastest Growing Agencies list in 2021, with more than 500% growth over the last four years, and was named as one of the top 15 platforms to watch in 2022.

We Are Rosie recently partnered with Align Capital Partners (“ACP”) to accelerate growth. To use our Founder’s words “We’ve reached the point where it would be a disservice to We Are Rosie’s mission and vision to throttle our growth by staying bootstrapped. This partnership provides us access to ACP’s growth resources and the capital to support our clients with better infrastructure so that we can accelerate our goals of creating access, opportunity, and wealth for independent marketers, especially those who’ve historically been marginalized by the industry.”


The Position

The CTO will collaborate with We Are Rosie leadership to establish the company’s technology product, application, and infrastructure strategy, and technical vision. This role is responsible for developing a technology roadmap, gaining buy-in from Rosie leadership and the Board of Directors, and then overseeing the execution and program management of all projects and initiatives dictated by those strategic plans. The CTO is responsible for building a secure, resilient, and scalable set of application platforms supported by underlying cloud infrastructure and automated integrations to enable the efficient and rapid growth of the organization. The CTO is responsible for delivering market differentiated customer digital experiences that reinforce the We Are Rosie brand/culture while building and growing an active social community of Rosies in the USA, and eventually globally.  The CTO needs to ensure that our IT platforms and processes can scale from our current 10,000 Rosies to 150,000 Rosies over a 3-5 year period. The CTO must lead a team that develops algorithms or other data-science capabilities that allow We Are Rosie to efficiently match and place Rosies at our B2B customers, while also surfacing insights about our match process, our customer satisfaction with our Rosies, and other data-driven insights that help We Are Rosie leadership make data-driven business decisions.

Tasks will include prioritization of projects/initiatives, recruiting/hiring, buy vs. build decisions, vendor negotiations and contracting, talent development, technical architectural design input and approval, data algorithm design input and approval, budgeting and forecasting of IT spend (Opex and CapX), and serving as an escalation point for the tech teams.

A key requirement is being able to collaboratively work with the We Are Rosie leadership, embracing the We Are Rosie culture and focus on inclusion, and always making decisions that support the Rosies in their career goals while simultaneously delivering the highest quality and diverse talent to our business Customers.


Key Responsibilities

  • Provide overall IT governance for the firm, in collaboration with the We Are Rosie leadership team and a potential future Product Manager role established at We Are Rosie
  • Plan, implement, manage and monitor changes in the overall IT infrastructure, cloud platforms, bespoke applications, and any integrations between cloud or bespoke applications and data mart(s). 
  • Build and maintain IT strategic roadmap(s) to clearly show how IT applications, integrations, data, and infrastructure will support the current and future needs of We Are Rosie business departments, Rosies, and Customers.
  • Architect all applications, cloud platforms, data, and infrastructure solutions to support efficient automated tasks to minimize manual tasks, while also supporting scalability and resiliency needed to support We Are Rosie growth plans for the next 3-5 years.
  • Hire and talent manage a dedicated IT team that can deliver on the IT strategic roadmap, while also finding and leveraging outside talent where needed to augment the team or to provide short-term specialized skills necessary to achieve specific goals.
  • Enhance our existing data mart with all data necessary to build and deliver an algorithm that improves our ability to match Rosies with our Customers to ensure great outcomes.
  • Ensure our data mart utilizes concepts for time series data, structured and unstructured data, direct or API or cloud iPaaS data feeds, and efficient data storage costs with multiple tiers based on concepts such as usage.
  • Serve as the top escalation point for any issues/outages that are unable to be resolved quickly by the team, and oversee in any resolution, root-cause analysis, and remediation.
  • Communicate with senior We Are Rosie management and the We Are Rosie Board of Directors on information technology plans, results, prioritization, and risks.
  • Manage all the IT staff, which includes hiring, training, coaching, developing, guiding, and discipline.
  • Actively manage risk mitigation plans to ensure Company Security, Data Privacy, Cyber Security, and Project Deadlines are appropriately managed and foreseen problems minimized.
  • Help the IT organization mature their development and testing procedures, moving towards a Continuous Integration/Continuous Development (CI/CD) environment.
  • Document and enforce IT policies and procedures, utilizing best practices for all infrastructure, security, applications, integrations, architecture, and maintenance/change control.


The Candidate

The ideal candidate will be passionate about the WRR mission and energized by the challenges and opportunities presented by rapid growth. They will be business-focused, proactive, fun, hard-working, detail-oriented, and creative leader with excellent judgment, self-awareness, and the ability to provide clear, balanced perspectives and insights on key Company issues.

  • Ideally brings a balance of big company scale and recent startup experience
  • Has operated and developed social cloud applications and scale
  • Has managed data science personnel responsible for developing algorithms that are utilized to improve business performance
  • Experience leading multiple simultaneous projects across applications development, vendor implementations, and infrastructure
  • Experience working with diverse working groups, and building diverse teams
  • Strong business experience especially around gaining executive/board buy-in to strategies, priorities, budgets, and risk mitigation plans
  • Proven cloud integration experience using iPaaS, API, or other scalable and common practices
  • A creative problem solver with remote work communication skills
  • A relentless desire to change the world for the better
  • A willingness and ability to roll up their sleeves and be a do-er across the function
  • A person aligned with We are Rosie core values:
    • We are in the business of entrepreneurship
    • We use common sense
    • We pursue growth
    • We are inclusive
    • We speak plainly
    • We trust you
    • We really care


What’s the Interview Process?

The interview process for candidates will involve meeting with core team members via video conference. We like to ask behavioral and situational questions that are aligned with the job requirements and our core values. The team will give you a look at the ideal day and what success looks like for the role. PS: We love questions!

We Are Rosie focuses on our 4P’s for human vetting methodology to validate candidates and assess soft skills. We believe that a combination of these factors makes a successful Rosie team member. 

  • Pedigree: Your work history and experience
  • Potential: Your strengths, tendencies, and acquired skills
  • Passion: The work you love the most 
  • Play: When, where, and how you like to work 



More about We Are Rosie!

We Are Rosie is a flexible talent marketplace for the advertising and marketing world. A thriving community of 10,000+ independent marketers, it helps companies like Bumble, Meta, IBM, Microsoft, and more leverage curated, on-demand teams and flexible marketing talent — while offering weekly pay and benefits. For more information, visit


More about Align Capital Partners!

Align Capital Partners is a growth-oriented private equity firm that partners with business owners and management teams to create shared success. ACP makes investments in differentiated companies that operate within the business services, technology, specialty manufacturing, and distribution sectors. ACP manages $775 million in committed capital with investment teams in Cleveland and Dallas. For more information, visit

We Are Rosie is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, age, national origin, ancestry, physical or mental disability, medical​​​ condition, pregnancy, genetic information, gender, sexual orientation, gender identity or ​expression, veteran status, marital status, or any other status protected under federal, state, or local law.