Customer Enablement Associate Jobs (NOW HIRING)

The Brydon Group is a Washington, DC-based private equity firm focused on acquiring and growing B2B, B2G, and Healthcare software and services businesses. Our portfolio companies typically generate $1–5M in EBITDA and $5–25M in revenue.

This is a high-impact role for a technically fluent operator who can translate AI capability into real business results. As our first dedicated AI Enablement leader, you will step into an entrepreneurial opportunity to build and lead our AI transformation capability — diagnosing opportunities, building and configuring solutions, and driving adoption across our portfolio companies.

You will report directly to the Partner overseeing Portfolio Operations and Value Creation and will work directly with portfolio companies, spending concentrated time at each business to drive meaningful change before transitioning to the next. In some periods you may support two to three companies simultaneously depending on portfolio needs and existing in-house capabilities.

This is not a slide-deck heavy role. We are looking for someone who will roll up their sleeves, build capabilities, drive lasting change and impact, and leave every business measurably better than they found it.

• Conduct structured operational assessments at each portfolio company: map workflows, identify manual and repetitive processes, surface pain points, and understand where humans vs. data are driving decisions
• Prioritize AI interventions based on ROI potential, implementation complexity, and business readiness — with a bias toward high-impact, MVP solutions to embed change quickly and iterate later
• Develop a clear, actionable roadmap for each company that aligns with management’s goals and Brydon’s value creation thesis

• Configure and deploy off-the-shelf AI tools where appropriate; identify gaps where lightweight custom solutions are warranted
• Integrate systems and connect data sources to enable AI workflows (APIs, Zapier-style automation, CRM/ERP connectors, etc.)
• Build and configure AI-powered productivity tools using platforms such as Claude, custom Claude skills/agents, and similar technologies to enhance job performance across functions (sales, operations, finance, customer success, etc.)
• Write code as needed — Python scripts, lightweight web tools, prompt libraries, workflow automations — to close gaps that commercial tools don’t cover
• Operate within tight budget constraints; creativity and resourcefulness are required

• Translate technical solutions into accessible, practical workflows that employees at all levels can use confidently
• Train and coach staff at portfolio companies; build internal champions and reduce dependency on external support over time
• Communicate clearly with CEOs, GMs, and frontline managers to align on goals, surface concerns, and maintain momentum

• Define success metrics before each implementation and track outcomes rigorously
• Follow up post-deployment to confirm impact, identify friction, and iterate

• Develop repeatable frameworks, process templates, and implementation playbooks that can be systematically deployed across current and future portfolio companies
• Codify case examples from each engagement — what worked, what didn’t, and why — into a growing library of institutional knowledge that compounds over time
• Stay current on the rapidly evolving AI landscape: new tools, models, platforms, and use cases — and proactively surface innovations that could benefit the portfolio
• Serve as Brydon’s internal AI subject matter expert, bringing best-in-class thinking to every new investment and value creation initiative
• Evaluate and manage external AI vendors, consultancies, dev shops, and/or contractors to extend 3rd party capabilities and speed of impact
• Build Brydon AI over time, expanding portfolio ops and value creation capabilities and capacity and collaborating across other internal Brydon AI teams and priorities

Requirements

• 3+ years of professional experience, with meaningful exposure to both technology implementation and business operations
• Background in management consulting, strategy, or operations — ideally at a firm that worked with small or mid-market businesses — combined with substantive technical experience
• Demonstrated, hands-on experience deploying AI tools in real business environments: not just advising on AI strategy, but building and launching solutions that people actually use
• Experience managing stakeholders and driving organizational change in companies that weren’t asking for it

• Proficiency in Python or another scripting language; comfortable building small tools and automations from scratch
• Working knowledge of APIs, webhooks, and integration patterns (REST, Zapier, Make, or similar)
• Familiarity with AI/ML concepts, LLMs, and prompt engineering; experience configuring tools like Claude, GPT, or comparable platforms in applied business contexts
• Ability to connect disparate systems and data sources without large engineering teams
• Degree in Computer Science, Engineering, Information Systems, Applied Math, or a related technical field preferred; equivalent demonstrated experience considered

• A tinkerer at heart. You build things to understand them, test constantly, and enjoy the process of figuring things out
• Structured and analytical thinker who can quickly identify what matters in a messy, resource-constrained environment
• Strong communicator who earns trust with skeptical operators and non-technical employees
• Comfortable working in ambiguous, standalone environments with minimal infrastructure or support
• Creative problem-solver who finds ways to do more with less

Benefits

• Compensation will be commensurate with experience and is expected to range between $150,000 to $250,000 OTE
• Brydon employees are eligible for paid holidays, health insurance and 401(k) retirement benefits
• This role is located in person, on site - based out of our Washington, D.C. office

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