Forward Deployed AI Strategist, Enterprise | Midwest

EvenUp is on a mission to close the justice gap using technology and AI. We empower personal injury lawyers and victims to get the justice they deserve. Our products enable law firms to secure faster settlements, higher payouts, and better outcomes for victims injured through no fault of their own in vehicle collisions, accidents, natural disasters, and more.

We are one of the fastest-growing vertical SaaS companies in history, and we are just getting started. EvenUp is backed by top VCs, including Bessemer Venture Partners, Bain Capital Ventures, SignalFire, and Lightspeed. We are looking to expand our team with talented, driven, and collaborative individuals who seek to have a lasting impact. Learn more at www.evenuplaw.com.

This role is explicitly designed for Tier 1 strategy consultants (Bain, McKinsey, BCG, etc.) who are technically capable and curious, want deep exposure to enterprise-grade generative AI, and are excited to move into high-impact SaaS GTM at a $2B+ valued vertical AI leader.

What You’ll Do

• Embed directly with Managing Partners, Directors, and practice leaders at sophisticated personal injury firms and become their trusted AI strategist

• Develop a sharp, opinionated point of view on product direction and roadmap – you will influence features daily based on real frontline usage and feedback from the most ambitious firms

• Master EvenUp’s proprietary multi-model AI platform and the full stack underneath it: advanced RAG architectures, specialized OCR + layout-aware extraction, annotation pipelines, fact / causation / treatment gap detection, medical bill intelligence, and agentic workflows

• Solve novel, high-complexity customer problems by composing models, prompts, retrieval strategies, and post-processing logic

• Design and deploy elegant, scalable solutions that deliver outsized value to customers while rigorously controlling cost-per-case and margin

You will spend the majority of your time building things with clients – prototyping solutions, tuning retrieval, designing new pipelines, and pushing the platform’s capabilities forward – not filling out onboarding checklists.

Role Requirements

• Prior experience at a top-tier strategy consulting firm or equivalent strongly preferred

• 50 - 80% travel within your coverage region

• 30% of total compensation is variable commission for successful customer trial conversion with opportunity to exceed on-target earnings

• Total project ownership for 90 day initiatives

• Genuine excitement about generative AI – you should enjoy going “under the hood”

• Exceptional communication and presence with every level of a customer organization – you will be navigating influence within orgs from the paralegal to the named partner

This is one of the highest-leverage ways to get extremely deep, hands-on experience with cutting-edge applied generative AI while directly driving revenue and product direction at an exceptional vertical SaaS/AI company.

Notice to Candidates:

EvenUp has been made aware of fraudulent job postings and unaffiliated third parties posing as our recruiting team – please know that we have no affiliation or connection to these situations. We only post open roles on our career page (evenuplaw.com/careers) or reputable job boards like our official LinkedIn or Indeed pages, and all official EvenUp recruitment emails will come from the domains @evenuplaw.com, @evenup.ai, @ext-evenuplaw.com, [email protected] or no‑[email protected] email addresses.

To ensure fairness and proper consideration, we do not accept resumes or expressions of interest via email or social media messages. If you’re interested in a role, please submit your application directly through our careers page.

If you receive communication from someone you believe is impersonating EvenUp, please report it to us at [email protected]. Examples of fraudulent domains include “careers-evenuplaw.com” and “careers-evenuplaws.com”.

Benefits & Perks:

As part of our total rewards package, we offer attractive benefits and perks to our employees, including:

• Choice of medical, dental, and vision insurance plans for you and your family

• Additional insurance coverage options for life, accident, or critical illness

• Flexible paid time off, sick leave, short-term and long-term disability

• 10 US observed holidays, and Canadian statutory holidays by province

• A home office stipend

• 401(k) for US-based employees and RRSP for Canada-based employees

• Paid parental leave

• A local in-person meet-up program

• Hubs in San Francisco and Toronto

Please note the above benefits & perks are for full-time employees

EvenUp is an equal opportunity employer. We are committed to diversity and inclusion in our company. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.