Strategy & Operations Associate

Rejigg•Chicago, IL

2d•$135,000•Onsite

About The Position

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

Requirements

Based in 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.

Nice To Haves

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.

Responsibilities

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.