Head Of Sales - Dear Media - New Way to Podcast


Head Of Sales

Dear Media is seeking a Head of Sales with an entrepreneurial spirit to lead advertising and sponsorship deals and partnerships for Dear Media.

The ideal candidate…


  • Lead the day-to-day sales and sales support teams for Dear Media’s podcasts, live events, and related initiatives.
  • Work with the leadership team to develop and achieve ad and sponsorship revenue goals and strategies.
  • Sell not individual shows but the network, with a focus on building long-term brand relationships.
  • Collaborate with the marketing team to develop integrated marketing plans for brand advertisers.
  • Participate in the development of marketing and public relations plans for the network, podcasts, content published across social video platforms, live events, merchandise, and consumer product advertising.
  • Work collaboratively with the talent, development, production, content, casting, business, sales, and legal teams to shape and implement the overall strategic plans for Dear Media.


  • Proven expertise and experience working in digital ad sales – at least 8 years of experience ideally in a primarily digital media company.
  • Deep relationships with brand advertising decision makers.
  • Nuanced understanding of the current ad sales marketplace and the ability to help create and sell sponsorship packages that go beyond narrow performance metrics.
  • The ability and desire to be part of teams at early-stage startups.
  • Strong knowledge of and passion for media largely created by and for women.
  • Awareness of pop culture trends in podcasting, video/television, publishing, music, digital, e-commerce, and social media broadly.
  • A network of talented sellers and people in sales support roles to draw on as we build our team.


  • A world-class salesperson.
  • Someone with a strategic view and the ability to assess risks and opportunities.
  • Able to balance revenue objectives with fidelity to and care for the Dear Media brand.
  • A leader capable of influencing through trust, communication, logic, and a constructively critical approach.
  • A grounded, collaborative team player.
  • Someone whose core values are integrity and honesty and whose colleagues describe her/him/they as a problem solver with a “get it done” approach.
  • A good business partner with the EQ and communication skills to balance creativity with data-informed decision-making.
  • Someone who engages in the process of getting to a decision – then when a decision is made, jumps in the boat with the team and rows in the same direction.
  • Someone who wants to both roll up sleeves and do the work while building a team capable of doing the same.

Success Requires That…

  • You are a direct communicator and welcome direct communication.
  • You love to win.
  • You want to get your hands dirty.
  • You solve problems.
  • You are entrepreneurial, smart, and passionate.
  • You naturally go the extra mile.
  • If you don’t know something, you say so. Then go figure it out quickly.
  • You give credit where credit is due and take responsibility for misses.
  • You love working in a creative environment.
  • You are a collaborator.
  • You know there’s more than one way to solve a problem and work hard to find the solution that works best for the company, team, and our partners.
  • You get – and can work in an environment where – often getting to 80% confidence and just going is the best strategy.
  • You have a sense of humor. Seriously.
  • You speak in plain language so the room can understand what you’re communicating.
  • You are an insatiable learner.
  • You are a good human.


  • Robust benefits package with employer contribution
  • Unlimited vacation time
  • WFH flexibility
  • Paid parental leave
  • Volunteer opportunities
  • Casual dress code & open office environment
  • A rewarding career at an industry-leading company with a strong mission and passionate team

Dear Media is committed to creating a diverse environment and is proud to be an equal opportunity employer. All qualified applicants will receive consideration without regard to race, ethnicity, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. Dear Media offers parental and family leave along with generous health and dental benefits for all employees.


Dear Media (DM) is the largest podcast network focused on strong female voices and audiences. Founded in 2018, DM hosts 40+ podcasts fronted by top-tier talent and has a following of more than 25M across social channels. DM is building the podcast network of the future through a 360 degree business model, providing unparalleled support from concept to editorial, production, distribution, and commerce extensions. Due to its highly engaged and vast consumer audience, the network attracts global brands and digital savvy partners including American Express, Adidas, Fossil, Bloomingdales, Nordstrom, Neiman Marcus, Maybelline, Chevrolet, Fabletics, Microsoft, and LinkedIn. Highly Crafted. Compelling Voices. Experience Dear Media.


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