2020 On-site is growing fast, and always hiring. We are a fun team driven by our mission to change the way healthcare is delivered. We work hard, but we play hard, too. If you want to work as part of a dynamic, fast-paced team and make a real impact in an innovative company, we want to hear from you.

Some perks include:

  • Free eye exams and discounted eye wear (duh)
  • Health, dental, life & long-term disability insurance
  • Casual Fri everyday
  • Swag
  • Monthly happy hours & beer Fridays
  • Foosball table
  • Seltzer water supply
  • Free snacks
  • Gym membership discount
  • Pre-tax commuter benefits



Are you the top producer on your sales team and eager to run a region? Are you a true entrepreneur looking to make a bigger impact? Are you a consummate networker and relationship builder? Do you excel at making strong in-person connections with influencers and decision makers? 2020 On-site is seeking high energy Enterprise Account Sales Managers with previous experience selling a robust solution in a fast paced environment.

As an Enterprise Account Sales Manager, you will identify and cultivate new business opportunities by driving strategic HCM initiatives within enterprise size organizations containing. You must be able to effectively work with internal and external partners, independently manage a full sales cycle, and accurately forecast sales while managing a pipeline four times your assigned quota. At 2020 On-site you will have the opportunity to sell our high-end on-site eye care services to C-level Executives without vertical boundaries. You will be able to grow your own business while still having the support of exceptional sales leadership, dedicated customer support, advancement opportunities, and industry-leading compensation, benefits and rewards.


● Consistently achieve/exceed an annual sales quota; selling to both new accounts as well as existing 2020 On-site clients. Must be proficient in both elements.

● Develop and execute territory business plans to define your strategies and tactics for success

● Develop strong relationships and collaborate closely with internal channels and product partners;

● Optimizing “center of influence” to best fit client needs during the sales process.

● Ability to work independently as well as collaboratively with a team to drive 2020 On-site Eye Care expansion with new/existing clients.

● Expand your network by working with external partners to gain access to industry knowledge as well as other key C-Level decision makers

Skills & qualifications:

● Minimum 3-10 years of relevant experience in HCM, benefits, technology, outsources services or software sales

● Bachelor’s degree or higher required

● In depth understanding of strategic sales processes or target account selling

● Strong communication skills and can effectively present to both C-suite level executives and mid-level associates

● Ability to leverage social media to promote thought leadership ideas and drive business development opportunities in your local market

● Utilize established network connections

● Solid business acumen with the ability to understand multiple industry issues and potential ways 2020 On-site can assistClick here to apply


Do you want to provide patient care in an exciting, fast-paced and dynamic environment? Welcome to the 2020 Onsite team! As an optometrist working with us you will be integral to creating a customer-centered experience in our mobile eye clinic. 

Because the patient is core to everything we do, you will have access to the latest most cutting edge equipment including an electronic refraction system and non-mydriatic fundus camera among others. Because we believe you should operate at the top of your license, you will have technicians assisting you with patient workups. Our set-up is a hybrid of a medical office with a retail optical shop supported by a retail manager. Our clientele consists of professionals from every industry sector ranging from e-commerce to finance and law. 


This position requires an enthusiastic and motivated personality with a penchant for the entrepreneurial environment. Candidate must have:

  • The ability to efficiently manage time and communicate clearly/professionally is crucial

  • Ability to expand and grow the business through internal corporate referrals

  • Transition patient in a seamless fashion from the exam lane to the retail shop

  • Create a culture of excellence that is patient centered

  • Prior clinical experience is preferred but not required

  • License to practice optometry in Massachusetts & Bachelors required 

Candidates can expect a highly competitive compensation package commensurate with experience.

Please email medicalcareers@2020onsite.com to apply.



Are you competitive and self-motivated? Do you have previous sales experience or a high degree of interest in learning sales and business development? Are you looking to learn from and grow with a rockstar team? We are looking for a motivated, self-starter to join our team as a Business Development Associate. We’re looking for someone excited to join a young team doing big things. You’ll gain professional experience at a startup, developing and implementing customer acquisition strategies and helping to bring on board first-time companies as well as repeat business. Our sales team is truly the lifeline of our business!


  • Ability to develop and maintain customer and partner relationships through outbound prospecting and follow up
  • Conduct medium-high volume phone and email prospecting for qualified leads
  • Demonstrate the ability to identify key players and decision makers in the buying process
  • Achieve team booking quotas by prospecting, identifying and helping to close strategic deals
  • Represent 2020 and local and regional events surrounding corporate wellness, health benefits, etc.
  • Analyze sales reports and pipeline reports to inform sales strategies and outputs


  • 1+ years of experience in an inside sales position required
  • Highly motivated
  • Comfortable being uncomfortable
  • Strong interpersonal and effective communication skills
  • Excellent time management and organizational skills
  • Carry high degree of competence in completing duties in a timely and effective manner
  • Must be a competitive, passionate team player
  • Strong understanding of customer and market dynamics and requirements
  • Strong desire to learn and work in healthcare sector, understand the intricacies of insurance and the existing health plan landscape in order to change behaviors
  • Bachelor’s Degree required

Please click here to apply.