Strategy & Operations Associate

Location: Chicago

Office: In-person (Friday WFH) in River North

Compensation: $135,000 base + equity package

Target start date: Feb - March 2026

Rejigg helps small business owners exit their companies by connecting them with qualified buyers. We’re building a more transparent, founder-friendly marketplace for business acquisitions — and we’re scaling quickly.

We’re hiring a Strategy & Operations Associate to be a flexible, high-ownership generalist. This is not a narrowly defined role: it will shift quarter to quarter based on what the business needs. We’re looking for an A-player who’s also a team player and who wants to roll up their sleeves and lean into working at a fast-growing, VC-backed, seed stage startup. You'll work closely with Rejigg's co-founder, Alex (ex-McKinsey, HBS).

Think of it as a jack/jill-of-all-trades operator who can jump into different projects, learn quickly, and help turn ideas into reality.

Your work will change over time. Some months you might be deep in hiring support; other months you may be working on user interviews, or helping structure internal processes.

Examples of what you might own or support:

• Support monthly goal setting & retros
  Work closely with leadership to prepare agendas, gather inputs, organize docs, and ensure follow-ups actually happen. Help refine the process over time based on what’s working.

• Help run hiring processes
  Schedule and conduct initial screening calls for candidates. Help us build a strategic, well-organized hiring process, then step in to do screening calls and interviews, and keep our pipeline organized

• Support the leadership team in one-off analyses
  Help the leadership team examine emerging trends on the platform and quickly diagnose them. Put together simple slides that explain complex topics to the leadership team and broader company as needed.

• Assist with customer & user research
  Set up and occasionally join user interviews with buyers, owners, or partners. Help synthesize themes and insights into clear notes or short summaries. Use those insights to help shape experiments or improvements.

• Work closely with sales
  Partner with the sales team and founders to support day-to-day execution: maintaining pipeline hygiene, updating CRM data, pulling simple reports, supporting follow-up cadences, and helping implement lightweight process tweaks or tooling changes.

• Represent Rejigg externally
  Represent Rejigg at conferences and events around the country, coordinate with partners and ecosystem players in the space, and help ensure follow-ups and opportunities from those touchpoints are captured and acted on.

• General sales & operations support
  Pitch in on outbound or follow-up work during busy stretches. Help tidy up workflows, documentation, and lightweight processes so the team can move faster. Use basic SQL and internal tools to pull simple metrics and answer questions.

• Special projects
  Work side-by-side with leadership on one-off or short-term initiatives as they emerge (new partnerships, internal experiments, product or ops tweaks, etc.). Take ambiguous ideas and help break them into clear, actionable tasks and timelines.

• Based in Chicago or willing to relocate to Chicago and able to work in-person with the team 4-5 days a week at our River North office.

• Willingness to travel 1–2 times/month for 2–3 nights at a time.

• Comfort with ambiguity and change
  You’re okay with the role evolving, priorities shifting, and jumping between different types of work.

• Strong generalist / project support skills
  You’re organized, follow through on details, and keep moving things forward without needing a lot of hand-holding.

• Very basic familiarity with SQL
  Enough to run simple queries, tweak filters, or learn quickly with some guidance.

• Clear written and verbal communication
  You can write a clean email, summarize a conversation, and ask good questions.
  

• Experience in management consulting, investment banking, or another analytical, project-driven role.

• Background as a search fund entrepreneur or exposure to SMB acquisitions.

• Prior experience in a sales operations, or revenue operations role.

• Experience in a startup, marketplace, or other fast-growth environment.
  

• Alex (one of Rejigg's co-founders) and the leadership team rely on you as a go-to problem solver who can pick up new projects and get them unstuck.

• Our monthly goals and retros feel organized, consistent, and action-oriented.

• Hiring processes run more smoothly: candidates are screened thoughtfully and move through the funnel cleanly.

• User and customer feedback is captured and synthesized in a way that’s easy for the team to act on.

• You’ve built enough context about Rejigg that you can anticipate needs and proactively suggest where you can help.