Sr. Director of Sales

You will have the unique opportunity to grow and develop a top notch sales team, structure the team and its processes for scale and success, refine Popular Pays’ positioning in a highly competitive market and elevate our conversations by leveraging your existing network. This is an exciting opportunity to step into an organization with a strong book of existing business and huge growth potential. We don’t want to grow any sales team - we want to build a cohesive, creative, solutions oriented, passionate team - we want to be known in the industry as a team that can be trusted implicitly, is able to provide cutting edge solutions for brands and agencies and is fun & transparent to work with. A dynamic and seasoned player/coach will grow the current team to new heights and make an immediate impact on strategy, process and sales success.

  • Oversee overall sales efforts and team (currently includes 7 direct reports) and ensure individual and company wide revenue is consistently growing. You will be responsible for the company wide book of business but will not be growing or maintaining an individual book of business. 
  • Own the hiring process/strategy and scale the sales team from 7 to 15+. (Current goal is 6 new reps in 6 months.) 
  • Consistently train and develop members of the sales team, ensuring they have a career path and personal growth plan that aligns with their personal goals and passions. 
  • Work in tandem with Head of Client Success & Partnerships to develop overall company revenue strategy, key account growth strategies and maintain goals and processes across both teams that allow for scale. 
  • Work in tandem with the Head of Marketing & Brand to build out marketing strategies that contribute to revenue (ie: lead generation for mid market brand, PR initiatives, brand facing materials and emails being utilized by your sales team) 
  • Develop/refine processes and structures within the sales team that will aggressively increase the company’s market share and the efficiency of the sales team. 
  • Own team and individual goal setting, as well as set and own commission structure for the sales team. 
  • Be data driven - own forecasting, pipeline tracking, quarterly and monthly reporting. Work to identify other KPIs and key business metrics that indicate we’re on track to meet our goals and unearth areas we can improve upon (on an individual level and as a team) 
  • Proactively leveraging your existing network and new contacts to grow the company’s profile within the industry 
  • Work as part of the leadership team to set overall company goals and vision, enacting change within the your own department and making cross functional recommendations to ensure the continued growth of company revenue.

  • Minimum 10 years experience successfully selling advertising solutions and growing teams and revenue with an ad tech firm, publisher and/or agency. 
  • Proven experience building a cohesive, high performing, trustworthy team of individual contributors. 
  • You are well connected within the advertising industry and bring senior level contacts to the table from existing agency and brand direct relationships. 
  • You understand and have built the structures required to guarantee success and create room for scale within enterprise level and mid market sales channels. 
  • You have been both strategic and very hands on in the success of teams you’ve been part of. 
  • You created and executed a team wide sales plan which resulted in significant growth. 
  • Excellent coach - you are honest, creative, solutions oriented and motivating. - 
  • You set your teams up for success and are relentless in ensuring there are no roadblocks to them meeting and exceeding their goals. 
  • You have worked closely across functions at your previous organizations to ensure your solution set has evolved based on needs in the marketplace that you surfaced. 
  • Ideally you have startup experience or experience building a new revenue stream or team within a larger organization. Your entrepreneurial mindset means you’ve worn multiple hats and helped drive our overall results, not staying limited to sales. 
  • You are a stellar communicator, both internally and externally. 
  • As a person, you’re patient, honest, motivated, a great listener, intuitive and want to work with an organization that is building a tech driven product and a unique culture that is rewarding to work within.

  • Talented teammates + access to the Y-Combinator network 
  • Work when it works for you, with flexible work hours and a generous vacation policy 
  • Paid trip for two for your two year work-anniversary and a paid sabbatical after 5 years 
  • Subsidized health care for you and your dependents 
  • Nutritious & delicious lunches catered every day 
  • Fully stocked pantry with snacks, coffee, tea, and more 
  • A fresh laptop, noise-cancelling headphones, & a motorized sit/stand desk 
  • An amazing office in the West loop with an inspiring view of Chicago.