Vice President of Sales

We didn’t create Bold Penguin because commercial insurance is broken. It isn’t. But as the world has gotten more connected and digitized, commercial insurance lags behind - creating a fragmented landscape where businesses, agents, and insurance companies struggle to interact in a smooth and easy way. That’s why we’ve built a highly efficient exchange that cuts the friction out of commercial insurance by connecting everyone to the right quote in record time.

Powering the world of insurance is no small feat, so we’ve brought on a team that's not only incredibly talented but also passionate about our potential to upgrade the entire industry. As more and more companies, big and small, depend on our technology to operate in the commercial insurance space, we’ll need the best talent all around to support our growth. That’s why we’re looking at you (yes, you!) to make a bold move and join our adventure.

Your Role

Bold Penguin is seeking a talented Vice President of Sales to expand our national partner base. The position will focus on leading sales for our suite of products and will report to the Chief Operating Officer. This requires driving the entire sales cycle, from establishing initial contacts and presenting the Bold Penguin solution, to closing the sale and engaging our Implementation team. 

What You'll Do

  • Responsible for the overall growth and success of client initiatives.
  • Manage client contracts from initiation and negotiation to delivery, working with internal and external parties to execute.
  • Develop and respond to RFPs and RFIs, collaborating with internal teams on responses. 
  • Assist in building business plans for future customers.  
  • Prospect, develop, and close new business, manage a robust sales pipeline, and deliver product demos and presentations to client executive teams.
  • Attend conferences, trade shows, and industry events, and execute go-to-market strategies via targeted campaigns and sales channels. 
  • Drive sales process, including scoping, pricing, and ROI calculations.
  • Collaborate and work with internal product, marketing, and engineering teams. 
  • Establish relationships with executive suites’ for targeted initiatives.  
  • Utilize internal CRM (Salesforce) effectively to record all sales activities, from prospect to close.
  • Manage and grow the sales team, leading sales meetings, conducting 1:1s, and delivering performance reviews.
  • Successfully transition closed contracts to the Implementation team. 
  • This role requires extensive travel within the U.S.

Skills AnD Qualifications

Required for this Position:

  • Extensive background in insurance.
  • Expertise selling enterprise software. 
  • Successful leadership of a team to achieve sales objectives
  • Experience working in a B2B fast scale growth company. 
  • Executive presentation and communication skills.

Additional Key Qualifications:

  • Experience working with leading insurance company executive suites, managing relationships with top carriers, brokers, and MGAs.  
  • Ability to build presentations, proof of concepts, and proposals, as well as other forms of formal communications as needed. 
  • Skilled in breaking down complex problems into actionable steps.
  • Knowledge and understanding of the marketplace and competitor offerings.
  • 12+ years of experience and 5+ years managing a sales team. 
  • Entrepreneurially-minded, a true self-starter.
  • Skilled at negotiating business terms with stakeholders and executive suites.
  • Ability to work in a rapidly expanding and changing environment.
  • Successful history of net new business.

Bonus Qualifications:

  • Bonus points for Insurtech background or commercial insurance experience!
  • Previous experience working at a brokerage a plus!


Preferred, but not required

Interpersonal Skills

Salary & Benefits

Bold Penguin believes in inclusion. That’s why we’re proud to be an equal opportunity employer that considers all qualified applicants regardless of race, color, religion, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, beak size, or inability to fly.

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