About the Role: 

We're looking for a talented CRM & System Administrator to own, optimize, and scale the backbone of our go-to-market and customer operations. This isn't a "keep the lights on" role -- it's an opportunity to shape how a fast-growing healthtech company runs its most critical systems. If you're someone who gets excited about clean data, smart automation, and building systems that make people's jobs easier, you'll thrive here. 

About the Team: 

You'll sit at the intersection of Marketing, Sales, and Delivery Operations -- partnering with leaders across the business to solve real problems through technology. As an individual contributor, you'll have a high degree of ownership and autonomy, with direct visibility to leadership and the opportunity to shape how we scale our CRM and systems infrastructure as the company grows. 

What You’ll Do: 

Platform Management & Optimization 

• Maintain and optimize HubSpot Marketing, Sales, and Service Hubs 

• Build and refine workflows, automation, sequences, and lead routing 

• Create and manage custom properties, pipelines, dashboards, and reports 

• Conduct regular data audits to ensure accuracy, cleanliness, and governance 

Platform Ownership 

• Configure and maintain tickets, pipelines, SLAs, and customer feedback surveys 

• Partner with client-facing and back-office teams to streamline ticketing processes and improve response workflows 

• Build automation that enhances customer experience—ticket routing, escalation rules, satisfaction surveys, and follow-up sequences 

• Support campaign execution by building emails, landing pages, forms, and segmented lists 

Cross Functional Support 

• Collaborate with Marketing, Sales, and the Delivery Ops teams to translate business needs into scalable solutions 

• Train internal teams on HubSpot features, processes, and best practices 

Systems Integration & Technical Ownership 

• Manage integrations between HubSpot and other business systems 

• Troubleshoot technical issues, identify root causes, and implement long-term fixes 

• Work with internal teams and external vendors on system enhancements and API based integrations 

Reporting & Insights 

• Build dashboards and reports that provide visibility into funnel performance, customer lifecycle, and service operations 

• Track KPIs across marketing, sales, and service to support data driven decision-making 

• Recommend improvements to processes, automation, and data structure based on insights 

What You Bring: 

• 3–5 years of hands-on CRM administration experience, with deep HubSpot expertise in a B2B environment 

• Deep expertise in HubSpot workflows, automation, lifecycle stages, and lead/ticket management 

• Experience supporting Customer Success or Support teams using Service Hub 

• Strong command of CRM data structures, segmentation, and reporting 

• Experience managing integrations between CRM platforms and third-party business systems, including tools like Intercom and Jira 

• Comfort working with custom-coded elements including troubleshooting scripts, custom workflows, or API-based logic 

• A systems thinker who can translate ambiguous business needs into clean, scalable solutions 

• Excellent communication skills and the ability to simplify complex processes 

Bonus Points: 

• HubSpot certifications (Marketing Hub, Sales Hub, Service Hub)  

• Experience managing integrations between CRM platforms and third-party business systems 

• Background in healthcare, benefits, or a high-growth SaaS environment 

What Success Looks Like: 

A great HubSpot Administrator doesn't just maintain the system; they make it work harder for everyone. Success means a well-organized, scalable HubSpot instance built on clean, reliable data, smart automation that reduces manual work, and clear reporting that drives smarter decisions across marketing, sales, and service. 

Compensation: $92,000-$115,000

The Account Executive Role

As an Account Executive selling Individual Coverage Health Reimbursement Arrangement (ICHRA) to employers. Your primary objective will be to drive revenue growth by acquiring and retaining broker partnerships, who will partner with you to identify new employer opportunities. In addition, you will be responsible for identify employers who are interesting in ICHRA’s and working with their brokers, as needed, to close the deal. The following job description outlines the responsibilities and requirements for this role:

Responsibilities:

• Develop and execute a comprehensive sales strategy to establish and maintain relationships with health insurance brokers and employers in the target market.
• Generate leads through networking, referrals, and prospecting to build a robust pipeline of potential broker partners & employers.
• Conduct sales presentations, product demos, and trainings to brokers & employers on the benefits and features of ICHRA.
• Collaborate with marketing to develop and implement marketing campaigns that generate interest in ICHRA and drive lead generation.
• Negotiate sales contracts and pricing agreements with employers to close deals and ensure profitability.
• Provide exceptional customer service to employers and brokers to their satisfaction with ICHRA.
• Keep abreast of industry trends, regulations, and competitor activities to identify opportunities and threats.
• Monitor and report on sales performance to identify areas for improvement and adjust sales strategies accordingly.
• Lead and mentor junior sales executives to ensure they meet sales targets and effectively manage broker relationships.

Requirements:

• Bachelor's degree in Business Administration, Sales, Marketing, or related field.
• Proven track record of sales success for 3+ years in a B2B environment in the healthcare industry.
• In-depth knowledge of the health insurance brokerage industry, including brokers, carriers, and regulatory requirements.
• Excellent communication and interpersonal skills to build relationships with brokers and other stakeholders.
• Strong presentation skills to deliver compelling sales pitches and product demonstrations.
• Ability to work independently and collaboratively in a team environment.
• Strong problem-solving and decision-making skills to identify and resolve sales challenges.
• High level of organization and attention to detail to manage and document sales activities, pipeline progress, and contracts.
• Proficiency in MS Office and sales management software.
• Willingness to travel to meet with brokers & employers and attend industry conferences as needed.
• SaaS experience is a plus!

What it takes to join our team
At Take Command, we believe in three key traits that set up a foundation for success in all sales roles within our team:

• Coachability 
  • The health insurance industry is complex and constantly changing. We are looking for folks that are not only open to being coached to success but are able to take feedback and implement it quickly. The attitude of “Feedback is a gift” goes a long way!
• Work Ethic 
  • We are big believers in ‘‘Talent is overrated” and that those with True Grit will rise to the top quicker than those with an abundance of talent but fail to put in the necessary time to achieve their potential. You may  be familiar with Malcolm Gladwell's “10 000-hour rule,” asserting that the key to achieving true expertise in any skill is simply a matter of practicing, albeit in the correct way, for at least 10 000 hours. Do you have the hunger and desire to get to these 10,000 hours quicker than anyone else? 
• Attitude
  • Sales is full of setbacks and there will be more deals that don’t go your way, than close. Feeling comfortable failing with the attitude of “Failure is a steppingstone on the path to success” is what is needed to be successful in any sales role, especially in sales in a startup environment as we continue to learn from mistakes, iterate processes and continuously improve. We are looking for positive people to add to our team, that believe it isn’t success that leads to happiness, it’s happiness that leads to success.

Account Executive Salary: $105,000-$115,000 OTE ($60,000-$70,000 + $45,000 variable)

Enterprise Account Executive

The Enterprise Account Executive Role

As an Enterprise Account Executive, you will be responsible for driving revenue growth by selling Individual Coverage Health Reimbursement Arrangements (ICHRA) to mid-market and enterprise employers through strategic broker partnerships and direct enterprise engagement.

In this role, you will manage complex, multi-stakeholder sales cycles, build relationships with national and regional brokerages, and work directly with C-suite and senior HR/benefits leaders at large organizations. You will partner closely with brokers to identify enterprise opportunities while also proactively sourcing and developing strategic employer relationships.

This role requires a consultative, strategic sales approach and the ability to navigate large organizations, educate stakeholders on the benefits of ICHRA, and drive consensus across multiple decision-makers.

Responsibilities

• Develop and execute a strategic enterprise sales plan focused on acquiring and expanding relationships with large employers and national/regional broker partners.

• Identify and pursue enterprise employer opportunities through broker networks, outbound prospecting, and industry relationships.

• Manage complex sales cycles involving multiple stakeholders including HR leaders, finance teams, benefits consultants, and executive leadership.

• Deliver executive-level sales presentations, product demonstrations, and educational sessions to brokers and enterprise employer decision-makers.

• Partner with brokers to position ICHRA as a strategic benefits solution for large employers transitioning from traditional group health plans.

• Build and maintain long-term strategic relationships with key brokerages, consulting firms, and enterprise clients.

• Collaborate with marketing to support enterprise-focused campaigns, events, and thought leadership initiatives that generate qualified opportunities.

• Lead contract negotiations and pricing discussions for enterprise deals, ensuring mutually beneficial outcomes while maintaining profitability.

• Serve as a trusted advisor to enterprise clients and broker partners throughout the evaluation, implementation, and expansion process.

• Stay informed on industry trends, regulatory developments, and competitive landscape to effectively position ICHRA in complex employer environments.

• Maintain accurate pipeline visibility and forecast enterprise deals within CRM systems (HubSpot).

• Partner with internal teams including sales leadership, partnerships, product, and customer success to ensure smooth deal execution and long-term client success.

Requirements

• Bachelor’s degree in Business Administration, Sales, Marketing, or a related field.

• 10+ years of B2B sales experience, with at least 2+ years selling to mid-market or enterprise organizations.

• Proven track record of closing complex, high-value deals with longer sales cycles.

• Experience working with or selling through health insurance brokers, benefits consultants, or HR leaders.

• Strong understanding of the health insurance or employee benefits ecosystem, including brokers, carriers, and regulatory dynamics.

• Exceptional executive communication and relationship-building skills.

• Ability to navigate large organizations and multi-thread deals across multiple stakeholders.

• Strong presentation and consultative selling skills.

• Highly organized with the ability to manage large pipelines, long sales cycles, and strategic accounts.

• Experience using CRM platforms (HubSpot preferred) and standard sales tools.

• Willingness to travel to meet with brokers, enterprise clients, and attend industry conferences.

• Employee benefits experience strongly preferred.

What It Takes to Join Our Team

At Take Command, we believe in three key traits that set a foundation for success across all sales roles:

Coachability

The health insurance industry is complex and constantly evolving. We look for individuals who actively seek feedback, implement it quickly, and view coaching as a pathway to continuous improvement. The mindset that “feedback is a gift” goes a long way.

Work Ethic

We believe that grit and persistence outperform raw talent. Those willing to put in the work, stay disciplined, and continually refine their craft will rise the fastest. As Malcolm Gladwell’s 10,000-hour rule suggests, expertise is built through consistent and intentional practice. We value individuals who bring the hunger to put in the hours required to master their craft.

Attitude

Sales inevitably comes with setbacks. Enterprise sales especially requires resilience, patience, and persistence. We look for individuals who embrace challenges, maintain a positive mindset, and believe that failure is simply a steppingstone toward success. At Take Command, we believe happiness fuels success — not the other way around.

Compensation

Enterprise Account Executive Salary:
$125,000 – $150,000 base + variable compensation (OTE dependent on experience)