Sales Director (Insurance and Health Insurance)

Responsiv; Chicago (IL); On-site; USD 180,000 - 260,000; Full time

Job summary

Responsiv in Chicago is seeking a Sales Director to drive net new enterprise logos through direct and partner sales in regulated industries. You will become an expert in compliance workflows and risk management, building relationships at executive levels across legal, compliance, regulatory controls, and IT security.

You will own the sales process from lead to close, manage named accounts, articulate Responsiv's vision and roadmap, and navigate complex RFPs and deployment scoping.

Qualifications

• Minimum 5 years of quota-carrying experience in new business development for an enterprise software organization.
• Minimum 5 years in complex selling environment requiring multi-level, multi-threaded relationships, ideally in Insurance, Health, Financial Services and other regulated industries.
• Demonstrated, referenceable success in past positions where closing multiple large transactions ($100k+ per year) and owning lengthy sales campaigns in a fast-paced, consultative and competitive market
• Record of success in generating net new business with consistent overachievement of annual sales goals in logos and ARR
• Demonstrated experience working with highly regulated insurers, including CCOs and regulatory SMEs, across: Health & Managed Care, Property & Casualty, Life & Annuity, and/or Disability & Long-Term Care

Responsibilities

• Drive net new enterprise logos through direct selling relationships and co-selling with partners.
• Build pipeline around prioritized accounts and move clients through the funnel.
• Manage named accounts with executive-level relationships in legal, compliance, regulatory controls, and IT/information security teams.
• Understand each company’s business, technology footprint and AI priorities.
• Know how to sell Responsiv’s vision and roadmap to customers.
• Operate well in a fast-paced environment with defined SLAs and rapid iteration.

Skills

Quota carrying

Enterprise software

Complex selling

Insurance industry

Multi-level relationships

Closing deals

Job description

Responsiv Overview

Responsiv is building the leading regulatory operating system for compliance, legal, and risk teams. Too many compliance leaders are still stuck stitching together fragmented alerts, manual spreadsheets, inconsistent sources, and disconnected pieces of advice, just to figure out what a regulation requires them to do. Responsiv solves this end-to-end, giving teams the ability to:

• Build and manage their regulatory universe: Create and maintain registers of the complex laws, rules, and regulations that apply to their business, across every jurisdiction and regulator they answer to.
• Cut through the noise: Filter and route relevant regulatory alerts to the right owners, so teams focus only on the changes that actually matter.
• Turn legal text into action: Translate dense regulatory language into clear, actionable obligations and requirements.
• Find gaps before regulators do: Map new requirements against existing policies, procedures, and controls to surface gaps and recommend the changes needed to close them.
• Move from finding to fix: Automatically draft policy and control updates, and track remediation through a defensible audit trail.
• Get back to the business faster: Understand the regulatory context behind situations existing policies don't cover, so the business can keep moving.

We are entering the market at a genuine inflection point. Nearly half of compliance organizations still use no dedicated regulatory intelligence technology today, and this category now has the highest purchase intent of any compliance technology segment — yet buyers are rightly skeptical of vendors making big AI promises without proof. That's exactly why we built Responsiv — a market-leading platform designed to deliver high-impact, defensible results. There's a clear opportunity to become the trusted partner compliance teams need.

Backed by Greylock and OnDean Forward (Andrew Sieja, the founder of Relativity).

Sales Director Overview

You are responsible for driving net new enterprise logos through direct selling relationships, as well as co-selling with partners when appropriate. You will become an expert in the regulated industries where legal, compliance and regulatory workflows are a requirement.

Build pipeline based around our prioritized accounts and move clients through the funnel.

You will be assigned named accounts and expected to build strong relationships at a true executive level to drive the strategy in target organizations. Your ability to navigate and build relationships in these departments will be crucial: legal, compliance, regulatory controls, and IT/information security teams. You will be expected to actively understand each company’s business, technology footprint and AI priorities.

Have an excellent understanding of Compliance and how Responsiv fits in.

You are an expert on the industry and our product. Learn and understand the value proposition that Responsiv offers and help corporations translate that value in their legal and compliance programs. Using that knowledge, you will need to know how our platform competes in the market and differentiates us from our direct competitors, as well as our indirect competitors.

Manage the sales process driving opportunities to a close.

You have a deep network in Insurance. You will manage a lead to an opportunity and can own each step of the selling process, especially in intricate, detail-oriented phases such as robust RFPs and proof-of-concepts (POCs). You have the awareness and keen ability to draw your opportunities to a close through situational selling that will shape your prospects’ mindset towards Responsiv.

Know How To Sell Our Vision And Roadmap.

Responsiv is a strong platform that has enabled us to have an incredibly strong offering out of the gate. We also have a compelling vision and roadmap to execute on that vision. Our customers are buying into that future as much as the current product, so you have a clear understanding of how we are going to continue to create value in our market.

Operate well in a fast-paced environment.

Build competence in our industry and product. You will have high expectations for our team and of yourself as we expect to get work done with quality and speed. You will own the SLAs to respond quickly to prospect and customer questions, as well as internal colleagues. Your ability to adapt, shift and change quickly as the environment changes will give you an edge in your selling position as we are learning frequently and inserting improvements into our business and processes.

Qualifications

• Minimum 5 years of quota-carrying experience in new business development for an enterprise software organization
• Minimum 5 years in complex selling environment requiring multi-level, multi-threaded relationships, ideally in Insurance, Health, Financial Services and other regulated industries
• Demonstrated, referenceable success in past positions where closing multiple large transactions ($100k+ per year) and owning lengthy sales campaigns in a fast-paced, consultative and competitive market
• Record of success in generating net new business with consistent overachievement of annual sales goals in logos and ARR
• Demonstrated experience working with highly regulated insurers, including CCOs and regulatory SMEs, across: Health & Managed Care, Property & Casualty, Life & Annuity, and/or Disability & Long-Term Care

• Advocate like you're right. Listen like you're wrong. We communicate ideas with both passion and humility. We are all responsible for innovation and believe that ideas can come from anyone.
• Practice extreme ownership: With ownership comes accountability. Deliver on your commitments and take individual responsibility for the team’s successes and failures.
• Measure success: Having clarity on what success looks like is critical to its achievement. Make sure the measurements are meaningful.
• Make an impact: Iterate quickly. Speed over Perfection. Results over Activity.
• Do more with less: We value efficiency and resourcefulness. Quality is not dictated by the quantity of resources, but how effectively they are used.
• Celebrate the wins. Acknowledge the losses. Both are important signals to help us steer the ship. Give meaning to the hard work by recognizing the moments, milestones, stories and people in our joint success.