VP Health Insurance

| Remote
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About Gradient AI:  

Gradient AI is a fast-growing startup, bringing state-of-the-art Artificial Intelligence (AI) and Machine Learning (ML) solutions to the trillion-dollar insurance industry.  Founded in 2018, we are a well-financed, have raised approximately $28.5 million, and rapidly growing start up.  Our software-as-a-service platform provides bias-free, data-driven insights, enabling insurance companies to profitably run their business and expand their offerings to underserved people and markets.     

About the Role: 

We are looking for a Senior Director/VP to act as the General Manager (GM) for our Health Insurance division. As part of an industry-leading team, you will help empower our clients by delivering innovative and effective solutions. You will work closely with our leadership and staff to evolve strategic recommendations regarding our AI/ML product offerings. 

We are looking for someone to think strategically and work collaboratively with our technical, sales, and client services teams in our rapid expansion into the Health Insurance Underwriting and Health Insurance Analytics market. 


  • Manage our Health Insurance solutions from end-to-end 
  • Translate complex AI/ML modeling techniques and methodologies into real-world business terms for health insurance underwriting and pricing use cases 
  • Participate in the sales and client process as a subject matter expert, while also serving in a consultative role for strategic clients 
  • Serve as a critical communication liaison to ensure that our technical team of data scientists delivers what our clients want and need 
  • Oversee engagements and drive positive results for our clients through timely and accurate delivery of our solutions 
  • Help our clients understand how to best leverage and apply our solutions in their business operations to achieve optimal outcomes 
  • Play an active role in managing the development of a product, from end to end. 


  • Bachelor's or Master's Degree; 12+ years' experience working in a health insurance setting  
  • Deep subject matter expertise in health insurance across various sectors including carriers/payers, MGAs, brokers, TPAs, PEOs, etc 
  • Previous profit & loss (P&L) experience 
  • Experience developing health insurance pricing and product plans from the ground up 
  • Experience working with technical teams and underwriting/ actuary teams  
  • Experience managing and delivering products 
  • Exposure or genuine interest in how AI/ML can change the insurance industry  
  • Excellent client-facing presence and communication skills; experience leading and managing teams  
  • Analytical problem-solving skills and familiarity with statistical and database languages like Python and SQL are nice to have  
  • ASA or FSA certification is a positive, but not necessary 

What We Offer:   

  • A fun, team-oriented startup culture   
  • Generous stock options - we all get to own a piece of what we’re building   
  • Unlimited vacation days 
  • Flexible schedule that supports working from home   
  • Full benefits package including medical, dental, vision, 401k, and more   
  • Ample opportunities to learn and take on new responsibilities   

We are an equal-opportunity employer. 

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Technology we use

  • Engineering
  • Product
  • Sales & Marketing
  • People Operations
    • JavascriptLanguages
    • PythonLanguages
    • SqlLanguages
    • PandasLibraries
    • ReactLibraries
    • DjangoFrameworks
    • DockerFrameworks
    • FlaskFrameworks
    • JupyterFrameworks
    • KubernetesFrameworks
    • SparkFrameworks
    • TensorFlowFrameworks
    • AWS RedshiftDatabases
    • NoSQLDatabases
    • PostgreSQLDatabases
    • AWS (Amazon Web Services)Services
    • TableauAnalytics
    • PardotCMS
    • SalesforceCRM
    • ZoomInfoLead Gen
    • SlackCollaboration
    • ZoomCollaboration

An Insider's view of Gradient AI

How would you describe the company’s work-life balance?

Gradient AI supports work-life balance by letting local employees choose whether they want to work from home or come into the office. We can work remotely from anywhere in the US & adjust our schedules to accommodate life outside of work. Additionally, unlimited PTO, which allows us to travel, see family, & do things we enjoy is the cherry on top!


Senior Data Scientist

How do you collaborate with other teams in the company?

Being the lead recruiter at GradientAI I collaborate with with almost every department to understand their hiring needs, goals, and ways we can partner successfully. It's been great to get to know colleagues from Sales in the West Coast to local Engineers!



What makes someone successful on your team?

Collaboration and support amongst all members for the success of each individual is what makes our team successful. We are encouraged to listen and learn from one another by asking questions, giving and receiving feedback, and adjusting our approach every step of the way. We also support each other when working toward our goals


Sales Development Representative

How do you make yourself accessible to the rest of the team?

Being present and accessible for the Gradient AI team is incredibly important to me. I’m in our headquarters office regularly, often grab lunch with the team, and walk around to catch up with everyone. It’s also important for me to meet personally with every candidate prior to joining Gradient AI.



What are Gradient AI Perks + Benefits

Gradient AI Benefits Overview

Startup perks with big-company benefits. We offer competitive salaries, bonus plans, all-inclusive health care including medical, dental, & vision, 401k, an employee assistance plan, and equity participation. We also have unlimited vacation along with 11 paid holidays, MacBooks for every new employee, and much more!

Volunteer in local community
We had our first Women of Gradient AI Volunteer week last winter where the women of Gradient AI came together to give back and volunteer at a local nonprofit in their community.
Open door policy
OKR operational model
Team based strategic planning
Pair programming
Open office floor plan
Employee resource groups
Employee-led culture committees
Quarterly engagement surveys
Hybrid work model
In-person revenue kickoff
Summer hours
Employee awards
Flexible work schedule
Since we're in number of time zones we work core EST hours but understand employees may have other obligations and are flexible with schedules.
Remote work program
Coming into our Boston Headquarters is optional to give our employees flexibility. Most employees come in T/WTh for in office collaboration (and free lunch)!
Mean gender pay gap below 10%
Diversity employee resource groups
Women of Gradient AI Resource Group and more to come!
Hiring practices that promote diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Our Flexible Spending Account (FSA) helps employees cover out-of-pocket medical expenses with pre-tax contributions of up to 3,050 and $5,000 for dependents annually.
Disability insurance
We offer short and long term disability insurance.
Dental insurance
TriNet, our benefits provider offers dental plans through 4 carries with different plan options. In network preventive services are 100% covered in all plans.
Vision insurance
TriNet, our benefits provider offers coverage through 2 carriers with high and low options available with both depending on your needs.
Health insurance
Trinet, our benefits provider offers a number of different insurance plans that to suit you and your family's needs.
Life insurance
We offer company paid life and AD&D insurance.
Wellness programs
TriNet, our benefits provider offers discounts off wellness and health programs.
Mental health benefits
Financial & Retirement
Company equity
Performance bonus
Child Care & Parental Leave Benefits
Generous parental leave
Gradient AI offers 12 weeks of fully paid parental leave for new parents after a year of employment.
Family medical leave
Vacation & Time Off Benefits
Unlimited vacation policy
Paid volunteer time
Paid holidays
Paid sick days
Flexible time off
Office Perks
Commuter benefits
Gradient AI offers pre-tax commuter benefits for all employees.
Company-sponsored outings
Gradient has various team outings throughout the year and a companywide kick off in the beginning of each year.
Free snacks and drinks
Gradient AI has a fully stocked kitchen including unlimited snacks, coffee, tea and all of the flavored sparking water you can handle.
Some meals provided
If you choose to work from our Boston Headquarters we cater free lunch.
Company-sponsored happy hours
Home-office stipend for remote employees
Gradient AI offers all employees up to $250 to set up their home office.
Mother's room
Onsite gym
Professional Development Benefits
Job training & conferences
Gradient AI offers a professional development stipend so employees can continue their education.
Lunch and learns
Promote from within
Mentorship program
We have a buddy program where all new hires are assigned a tenured employee to help them ramp in their role and be a resource during their first 90 days.
Continuing education stipend
Gradient AI offers a professional development policy to help employees increase their skills and enhance their contributions to the organization.
Continuing education available during work hours
Customized development tracks
Paid industry certifications
Personal development training

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