Enterprise Value Strategist

About Dotwork:

Dotwork connects strategy, goals, capital, work, and outcomes in a live enterprise operating model — giving leaders and AI the context to make better decisions, adapt faster, and continuously improve performance. We bring portfolio management, enterprise business management, technology business management, IT financial management, FinOps, enterprise architecture and tokenomics together as one operating model. We define and build the answer with our customers, then hand them the keys.

Role Overview:

We're hiring people whose primary expertise is in one or more of these domains, and who also know how to get things built using AI as the primary means of production rather than writing every line by hand. You'll partner directly with customer leaders, diagnose how they run their domain, and build the solution on the Dotwork platform with them, from first prototype through production.

Core Domains:

• Portfolio Management: Strategic, Lean and Project Portfolio Management (SPM, LPM, PPM)
• Business & Finance: Enterprise Business Management, Technology Business Management, IT Financial Management
• Cloud & AI Spend: FinOps, Tokenomics
• Architecture: Enterprise Architecture Management

Who You Are:

• Courageous – You're willing to take on a problem before you have all the answers. You say what's true, and you admit it plainly when you don't know something or got it wrong.
• Committed – You make commitments to your team and your customers, hold yourself accountable to them, and say so plainly when you fall short. That commitment extends to your own growth, and to elevating the people around you.
• Connected – You value the work you do and the people you do it with. You want colleagues you trust enough to speak up around, who you can hold accountable and be held accountable by, and who push you to be better.

Key Responsibilities:

• Partner directly with customer stakeholders, paired with a specific counterpart on their team, to diagnose gaps in how they run their domain.
• Translate business and operational requirements into technical requirements and, where needed, solution architecture that AI-assisted development can act on.
• Configure and administer the Dotwork platform and the systems the solution connects to.
• Direct the build: prompt, review and iterate with AI tools to produce working solutions, from prototype through production.
• Apply real diligence to everything you build with AI. Read, question and verify the output rather than accepting it at face value.
• Demo what's been built. Show stakeholders the prototype or platform in action, and the value it drives.
• Present findings and recommendations to executive stakeholders in language they can act on.
• Maintain a current record of each engagement — documentation, deliverables, status, working information and learnings — throughout its lifecycle.
• After each engagement, look back at what worked and what didn't, and turn the repeatable parts into reusable skills, agents or workflows that improve the next engagement and the one after that.

Ideal Candidate:

• Deep Domain Expertise – Credible, hands-on expertise in at least one of the core domains above. This is the bar we hold highest.
• Business-to-Technical Translator – A track record of translating between business stakeholders and technical execution, in both directions.
• Comfort with Ambiguity – You take ownership of problems without a fixed playbook, and you're genuinely interested in finding a better way rather than repeating the known one.
• AI-Directed Builder – Working proficiency directing AI coding tools and configuring the platforms your work runs on: enough to build real things, read and verify what gets produced, and catch defects before they ship.
• Judgment & Decision-Making – You regularly decide whether work, human or AI-produced, is ready to put in front of a customer, and you document the reasoning behind consequential calls so others can follow it later.

Preferred Qualifications:

• Hands-on experience with agent frameworks or applied LLM tooling.
• Prior experience embedded directly with enterprise customers, in implementation, professional services or a similar capacity.
• Formal certification in at least one of the core domains.

What We Offer:

• A unique opportunity to combine deep domain expertise with building real solutions, using AI as your primary means of production.
• The chance to use cutting-edge AI tools daily, both in your personal workflow and integrated customer solutions.
• A collaborative and visionary culture where we want everyone to feel they're doing the most challenging, but best work of their careers.
• Competitive compensation, benefits, and a flexible work environment.