Head of Sales

Direct Hire Portland, Maine
  • Location: Portland , Maine
  • Type: Direct Hire
  • Job #17536
The Head of Sales is responsible for sales strategy and execution to drive the key revenue streams of the business, including new customer acquisition via direct selling, acquiring new customers via platform, service, trade association and other partner sales channels, and growing business with existing customers via upsells, cross-sells, further user utilization of our solutions. 

This role leads sales, account and partner management functions, and the successful candidate will have a demonstrated track record of success in meeting or exceeding goals for revenue growth and retention across the entire business. Deep expertise in building B2B SaaS sales strategies, and the ability to work collaboratively with the marketing team to execute on new business sales targets is also required. In addition, the successful candidate will have expertise directing an account management team to own the post sales experience, focused on driving “land and expand” revenue strategies with new and existing customers.

The Head of Sales integrates members of the team ranging from our CEO to Sales Engineers in order to deliver a valuable sales experience for prospects. They are responsible for establishing a lean and efficient sales cycle, as well as assisting in streamlining the sales to delivery handoff with members of the delivery team.


  • Develop strategy to drive new business and expand the existing customer base. You will communicate and own the execution of this strategy, including budgeting, scoping, setting targets, reporting on KPIs and collaborating with other teams to meet or exceed revenue targets.
  • Deliver the revenue committed to in the plan each month.
  • Mentor and coach Business Development Representatives and Customer Success Managers, optimizing the team to improve on their ability to acquire new revenue by generating, advancing and closing deals in the sales pipeline.
  • Assist Business Development Representatives and Customer Success Managers where necessary on larger revenue opportunities including; being involved in the sales process for new business, and helping manage existing accounts to drive account expansion and retention.
  • Own sales operations, and account management operations, including technologies, processes and systems (database management, segmentation, analytics, data cleansing, etc.).
  • Monitor and analyze performance against revenue growth goals. Continually make and implement recommendations for optimization and ongoing growth.
  • Working with the Head of Marketing to ensure the Sales team is receiving the Product Marketing and Demand Generation support they need to achieve their revenue targets.
  • Working with the Head of Implementation to ensure the onboarding and support functions are being optimized to improve the customer experience.
  • Manage the Head of Partnerships, to drive new customer acquisition and revenue growth via partner channels.
  • Working with the Head of Professional Services and Managed Services to identify and execute on new business growth opportunities with particular focus on new industries and verticals in which the business can pursue to unlock new revenues.
  • Communicate with senior leadership on an ongoing basis regarding revenue performance results, current initiatives, and course corrections being taken.
  • Establish and own sales cycle
  • Lead demos and pitches to a range of audiences from analysts to executives
  • Assist in streamlining sales to delivery handoff
  • 7+ years of Sales experience and demonstrated track record of success in meeting revenue and growth targets in a B2B SaaS business, managing sales budgets, developing and executing effective and efficient sales processes and methodologies, that maximize customer acquisition and drive desired business results.
  • Managed high performing B2B SaaS sales teams, with annual individual revenue targets in excess of $5M in new ARR.
  • Proven track record for delivering results, with ownership over key business metrics, and ability to take full responsibility in creating and executing on business growth strategies.
  • Demonstrated ability to think strategically & creatively, solve complex problems in a highly organized approach, as well as the ability to execute and effectively drive results.
  • Resourcefulness; ability to influence and collaborate with both internal team members and external partners.
  • Excellent analytical, communication, interpersonal and presentation skills. Must have initiative, and be action-oriented.
  • Team player with a collaborative approach who shares success.
  • Highly organized multi-tasker who strives for accuracy and is self-driven
  • Ability to prioritize multiple, competing priorities
  • Strong self-organizational, problem solving, and critical thinking skills
  • Strong communication and interpersonal skills
  • Knowledge of Business Intelligence
  • Creative and Innovative
  • Proficient with GSuite, Solution Selling and Hubspot (or similar CRM)
  • Bachelor’s degree
Preferred Experience:
  • Experience in selling Financial Services products
  • Experience in product sales and consultative approach to solutions selling
  • Work experience in a small, fast-paced environment
  • Sales process documentation and implementation
  • Experience in building out a successful and sustainable sales organization

Apply to: Head of Sales

Attach a resume file. Accepted file types are DOC, DOCX, PDF, HTML, and TXT.

We are uploading your application. It may take a few moments to read your resume. Please wait!

ProSearch is Maine’s premier staffing and recruiting firm. Our job is to connect great people with great opportunities. Established in 1994, ProSearch helps Maine’s top employers build their teams by recruiting just the right people – from temp/temp-to-hire, to IT consulting, to direct hire- for just the right positions.

ProSearch is proud to be an affirmative action/equal opportunity employer. All qualified applicants will receive consideration without regard to race, creed, gender/sex, marital status, sexual orientation, citizenship status, color, religion, national origin, age, disability, veteran status, or any other status protected under local, state or federal laws.