About SimplyInsured

SimplyInsured is on a mission to eliminate the fear from buying health insurance. We work with small business owners working to provide health benefits for their employees and their families. With over 7,000 customers and major partnerships with Intuit QuickBooks and Square, we're growing rapidly and disrupting a convoluted and confusing industry by making it more transparent and accessible. 

Our leadership team has founded companies; scaled successful startups like Cardpool and Domo; worked in established companies like Cisco Systems, Convergys, Dell EMC, and Yahoo; consulted at Bain, McKinsey and Deloitte; and invested venture capital. We got our start in the Y-Combinator incubator, and have been funded by top tier investors at Polaris Partners, Bessemer Venture Partners, and AltaIR Capital. 

We value radical transparency, feedback, bias to action, growth, and the obligation to dissent. Every opinion is respected, we hold each other to extremely high standards, we're driven by the diversity of our backgrounds and our complete alignment on our mission.

About the Role

You’ll help us hire, develop, and manage a team of 5-10 small business sales reps. You'll train and empower reps to identify and solve customer problems and eliminate fear from health insurance. You'll be a role model for our company values and our mission. You'll help us dramatically increase conversion on the extremely warm leads we're receiving from our Fortune 500 Partners, and build a vital piece of SimplyInsured's future success. You’ll work with a dynamic team of sales professionals, product experts, and leadership to help you excel in your career.

Day to Day Responsibilities

  • Build and lead a team of 5-10 sales reps to achieve and exceed weekly/monthly/quarterly targets
  • Encourage and empower your team to perform to their full potential. Build a world-class consultative sales team by investing in and developing the existing sales team while at the same time attracting top sales talent to SimplyInsured
  • Help refine and further develop our strategy: double the conversion of our world-class product with effective sales problem solving
  • Lead by example by rolling up your sleeves to embrace the phone, deliver demos, craft and refine messaging
  • Use data to inform decision-making and focus areas - ranging from AE skill development (e.g. coaching conversations, email campaign usage) to team initiatives (e.g. staffing to seasonality, piloting new activities). Track, measure and report-out on sales effectiveness against targets and adjust programs and strategies as necessary
  • Partner with cross-functional teams to refine lead targeting, messaging, lead qualification, and opportunity handoff
  • Build a culture of fun and excellence within the team. Cultivate each individual’s skill set development and guide career pathing as they grow within the organization
  • Collaborate with our Product and Customer Support teams to create amazing experiences for new SimplyInsured customers
  • Ensure the effective use of Salesforce.com and other tools

Ideal Candidate Attributes

  • 4-6 years of experience in Inside Sales, preferably in SaaS-based products and/or services
  • At least 2 years of shown quota-carrying experience as an individual producer
  • 2+ years of people management experience in a sales organization
  • Consistent track record of establishing and exceeding measurable goals
  • Experience with start-up environments and SMB SaaS sales models
  • Excellent working knowledge of inbound and outbound SaaS sales methodologies
  • A passion to pick up the phones and coach reps on consultative sales, qualification, and objection handling 
  • Ability to interact effectively with multiple teams: excellent social and interpersonal skills
  • Bachelor’s degree from an accredited university
  • Salesforce.com experience required

What We Offer

  • Competitive compensation
  • Lunch and Dinner every day (along with snacks and drinks)
  • Offsite retreats every 100 days - we have the ability and drive to iterate quickly and this helps us all stay on the same page and develop new ideas
  • 100% covered Medical, Dental, and Vision Insurance coverage
  • A values-based culture that invests in employee success
  • This role is currently remote due to COVID-19.  Candidates would be set up with a home office until it is safe to return to our office location. 

Apply for this Job

* Required