Chief Operating Officer

The Role:

Popular Pays is seeking a Chief Operating Officer who will drive the execution of company strategy.

As COO, you’ll collaborate with other members of the executive team to translate this strategy into actionable goals for each department, helping the company achieve and exceed short term targets while promoting our long term vision.

You’ll have the challenging but rewarding task of ensuring we execute on these goals and strategies to drive top line growth and our transition from campaign-based revenue to recurring SaaS revenue, implementing and iterating on internal operations systems to support these initiatives. 

Besides organization-wide goal setting and accountability, you’ll be the point person for functions like working capital, corporate and commercial legal, facilities, and compliance.

Ideal candidates will have a proven track record of operational excellence, preferably with experience at growth stage startups, in the advertising industry, and / or at SaaS companies.


In Year 1, you will:

  • Oversee the operations of the organization to meet business goals and projections.
  • Collaborate closely with the CEO and members of the executive team to drive department and company goals, operations & strategy.
  • Own accountability, working with the CEO and department heads to ensure each department’s goals promote growth, stay on budget, and are executed upon.
  • Work alongside our finance & accounting team to strengthen our operational efficiency, collections, audits, and liquidity management processes.
  • Help determine the sales and contract terms we take to prospective SaaS enterprise clients, balancing what will get the deal done with what puts our company in a strong position (e.g. payment terms) and limits the internal operational workload.
  • Manage and consolidate multiple internal systems for things like Salesforce documentation, invoicing, and revenue recognition, as we transition from campaign-based revenue to recurring SaaS revenue, making sure these processes enable growth instead of hindering it.
  • Review and improve how we invoice, collect from clients, pay our vendors, and manage our line of credit to strengthen our working capital position.
  • Negotiate contracts with clients and vendors, determining when to pull in our outside counsel, when we should compromise on certain terms, and how to document and manage these deviations from default terms.
  • Seek to streamline and quantify our legal process to better understand our legal throughput and how to get contracts from draft to signature as quickly as possible.
  • Create comprehensive analyses to identify which key drivers move the needle the most, informing company OKRs, driving decision making across the company, and generating results.
  • Identify and address bottlenecks for scale; lean in as problem solver for bigger challenges facing the company
  • Empower the executive team with the leadership and resources they need to successfully complete strategic initiatives.
  • Positively represent Pop Pays at all times through a success-oriented and professional demeanor.


Must Haves:

  • BA/BS in Business Administration or relevant field.  MBA/MS is a plus but not required
  • Familiarity with the operational procedures at all levels of the organization
  • Strong analytical and data-driven mindset that translates into results
  • Demonstrable competency in strategic planning and business development
  • 10+ years of industry experience, including demonstrated success in a leadership position
  • Ability to manage a high volume of tasks at once, outstanding organizational skills, attention to detail and ability to multitask in a fast-paced environment
  • Experience working with and leading cross-functional teams (Marketing, Finance, Product, Sales, Support, etc.) to be the voice of the company
  • Working knowledge of data analysis and performance/operation metrics
  • Outstanding organizational and leadership abilities
  • Excellent interpersonal and public speaking skills
  • Aptitude in decision-making and problem-solving


Ideal Candidate Traits:

  • You’ve led operations at a growth stage startup or for a company in the advertising and marketing space.
  • You have first hand experience at a SaaS company and have even helped a company manage the transition from episodic to recurring revenue.
  • You’ve owned organization-wide goal setting, performance management, and accountability to boost organizational outcomes.
  • You have tons of examples of operational systems you’ve put in place or existing ones you improved upon to support and boost business objectives.
  • You’ve worked with AR & AP teams and managed lines of credit and bring to the table best practices and systems to ensure our working capital position is healthy and supports the growth of the business.
  • You may not have a law degree, but you’ve reviewed and negotiated all sorts of business contracts and feel comfortable running point on legal conversations with both clients and vendors, looping in our outside counsel where appropriate. You even look forward to opportunities to negotiate to get us the best deal possible.
  • You understand the in’s and out’s of compliance, including things like federal and state requirements, benefits and insurance, and GDPR.
  • You are able to clearly communicate our vision to our board of directors, executive team members and company employees.
  • You possess the ability to inspire employees to live up to their potential and optimize their productivity.
  • You are a team player who rallies behind our team, customers, and creators and help them all succeed.
  • You are excited by the challenge of multiple decision makers and complex circumstances.
  • You are committed to curiosity and the ever-evolving world of Popular Pays & social media.
  • You are a doer and a grinder, ready to roll up your sleeves to tackle any problem that arises, whether it be above your pay grade or below.


Why You Should Work Here:

  • Influencer marketing and content creation industries continue to boom, and we think the opportunity beyond that is much greater – you’ll play an essential role in helping Pop Pays to chase down that opportunity, while shaping the next era of advertising and content creation in the process.
  • You’ll lend your talents and experience to solving really interesting and challenging problems that’ll drive meaningful impact for the industry, our users, and our company.
  • Collaborate daily with 40 top-notch teammates that collectively create a Culture Worth Sharing.
  • Work when it works for you, with flexible work hours and a generous vacation policy.
  • Comprehensive benefits package, including subsidized healthcare, dental, vision, life insurance, transit, and 401(k) plans.
  • Fully stocked pantry with snacks, coffee, tea, and more.
  • A fresh laptop, motorized sit/stand desk, and a massive monitor to take your spreadsheet game to the next level.
  • An awesome office in the West Loop, close to restaurants, bars, and public transit options.


About Popular Pays:

Global ad spend on influencer marketing is estimated to hit $5B+ by 2020, and the volume and variety of content needed by brands grows at an ever-increasing rate each year – McDonald’s CMO said they went from creating ~2.5k pieces of marketing content per year to ~5k per year, and that was back in 2016!

At Pop Pays, we’re building the operating system for collaborating with creators, to provide our clients the most robust all-in-one software solution for influencer marketing and social content creation.

Our platform connects creators with brands to generate content worth sharing - so shareable in fact, the fruits of these collaborations have been posted to billions of followers online, boosted to millions more via digital ads, repurposed for in-store menu boards, dropped into consumer’s mailboxes as part of direct mail campaigns, and featured amongst the bright lights of Times Square on billboards. A few more of our highlights:

  • Our company is a member of Facebook’s, Instagram’s, and Pinterest’s marketing partner programs.
  • Our CEO, Corbett Drummey, was named to Forbes 30 Under 30 for Marketing and Advertising in 2018.
  • Pop Pays is a Y Combinator alum – “the world’s most powerful start-up incubator” according to Fast Company.
  • Check out our Sizzle Reel, recapping some of the best content generated by creators on our platform last year – the video itself was put together by one of our creators!
  • Top-notch clients who have benefited from the Pop Pays platform include brands like Bose, Revlon, Coca Cola, Samsung, McDonald’s, Walmart, Valvoline, Jim Beam, M&Ms, Corona, Macy’s, and many more.

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