let’s build the future of work together

Head of Sales


We’re growing! We Are Rosie is hiring a Head of Sales!

  • 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 is a full-time position that can work from anywhere in the US and will report directly to our CRO.


The Company   

We Are Rosie (the “Company”) is the first flexible career platform for marketers and advertisers.  We are on a mission to bring about a more inclusive, flexible, human future of work.

Founded in 2018 with the mission to support extraordinary independent marketers in all seasons of their career, we provide a way of work that treats everyone with dignity and access to opportunity. Our community of 15,000+ “Rosies” makes it possible for forward-thinking brands and ad agencies to augment, complement, backfill, and accelerate their teams with a flexible layer of highly skilled talent and embrace remote/flexible work as a form of inclusion. We are working every day to thoughtfully disrupt the agency, consulting, and staffing models of marketing services.

We Are Rosie currently works with 20+ Fortune 500 brands, the big six agency holding companies, and smaller independent agencies. The Company is growing in excess of 100% year over year and has been featured in Business Insider, Campaign US, Forbes, and AdWeek and more. In addition, Stephanie Nadi Olson, our founder has been awarded 2022 EY Entrepreneur Of The Year – Southeast, one of Atlanta Business Chronicle’s Most Admired CEOs, 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.


The Position

As the Head of Sales you will champion our sales team in our year over year growth while establishing us as the premier partner for the world’s leading  companies by ensuring we support our clients in building amazing teams with our flexible elite talent, and as business partners. Your focus will be on developing our client directors and strategy to expand and engage our scope of the We Are Rosie Client portfolio, drive revenue, and ensure our Clients achieve outstanding scale, innovate faster, and transform.

The Head of Sales will focus on mutually-beneficial, long-term relationships that establish We Are Rosie as a trusted partner. You will help the world’s best companies change the way they build teams, get work done, and leverage the power of a blended workforce and distributed teams. You will work in a distributed company and help define an entirely new space helping the world’s best talent find the perfect opportunity while also helping leading organizations find the best talent more effectively and efficiently.

You will contribute & execute to building a client-building strategy, and effective processes for We Are Rosie. You will collaborate closely with our Client Operations, Talent, and Marketing teams to understand the key areas of growth within which we need to drive our mission forward. The Head of Sales will manage a team of Client Directors. You are a proven sales leader, that is responsible for driving accountability and that our Client Directors are paces towards our revenue goals.


  • Leads our Client Directors to surface the world’s best marketing opportunities for our Rosies community.
  • Grow and Sustain the WRR current client accounts to hit targets.
  • Manages prioritizing client needs to hit top-line revenue goals.
  • Accelerates growth in areas of greatest Rosie talent supply.
  • Develop Client engagement strategies.
  • Develop repeatable processes, and playbooks to ensure client success from the first touch point.
  • Take charge of recruiting and hiring a world class sales team.
  • Motivate sales team by providing feedback and recognition for behaviors that drive positive results.
  • Providing regular feedback to each member of the sales team regarding their performance.
  • Coaching team members on effective sales techniques and methods for increasing revenue.
  • Developing strategies to improve sales performance through ongoing training and development.
  • Develop sales training programs.
  • Develop & monitor sales activity metrics and performance and hold sales team accountable.
  • Ensuring that team members have the tools they need to succeed to drive targeted growth.


  • Strong verbal and written communication skills, proactive problem-solving abilities, and a collaborative mindset.
  • Experience leading & coaching a team.
  • You align with our core values.


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 15,000+ 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

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.