AI Investment Lead
About Bonside
Bonside is building the first brick-and-mortar credit platform. Multi-unit retail operators -- restaurants, fitness studios, service businesses -- form the backbone of local economies but have historically lacked access to capital designed for how they actually work. We changed that.
Our first product, the Repeatable Revenue Agreement (RRA), provides growth capital without dilution or personal guarantees, underwritten on the recurring, predictable revenue patterns unique to physical businesses. We are backed by leading investors in finance, technology, and brick-and-mortar and trusted by nationally recognized brands like José Andrés Group and F45.
The opportunity
The Investment Associate role will own every investment from initial handoff through presentation to our Investment Committee, make the call on whether we move forward, and quarterback every deal process. You are the accountable person on each deal, working directly with our Commercial and Capital Markets teams to support growing businesses every day.
We are a process-forward, AI-enabled capital platform. You will execute on our business diligence process and framework, while continuously improving it. A strong fit for this role is someone who has functioned as an Associate or VP-level deal lead, thrives on ownership, and wants their fingerprints on both the decisions and the infrastructure that powers them.
Who we are
- Ambitious: building a future where brick-and-mortar growth runs on Bonside
- Curious: operating in uncharted territory with a leave-no-stone-unturned mentality
- Collaborative: reaching clarity through team discussion and respectful pushback
- Backed by the best: supported by leading investors in finance, technology, and brick-and-mortar
What you will own
Deal Ownership & Investment Acumen
- Quarterback every deal end-to-end across from onboarding and diligence to Investment Committee -- you are the single accountable party
- Make investment recommendations with conviction; present and defend them at IC
- Drive deal velocity across your pipeline without sacrificing diligence quality
- Lead all business owner interactions during the review process -- calls, follow-ups, and data requests
- Develop and apply systematic risk assessment across business model, unit economics, and operator track record
Process & Automation Ownership
- Proactively identify and resolve process gaps that slow deal velocity or compromise data quality
- Build AI-based infrastructure that scales: new team members should be able to execute diligence using your frameworks
- Work across Retool and HEX tooling to improve data pipelines and analytical workflows, and drive the adoption of new AI tooling to further enhance our process
- Own the evolution and automation of Bonside's diligence framework
What we are looking for
- 3-5+ years experience across investment banking, private equity, private credit, direct lending, deal operations, or AI
- Demonstrated experience leading deal processes and adopting AI into your workflows
- Strong financial acumen and investment evaluation experience
- Exceptional written and verbal communication; you can translate complex analysis into a clear investment thesis
- Comfortable in client-facing conversations with business operators; professional, direct, and organized
- Bachelor's degree required; finance, business, or engineering preferred
- Genuine interest in brick-and-mortar businesses, alternative credit, and building something new
What success looks like
- Deal quality: your IC presentations are tight, well-supported, and reflect sound independent judgment
- Framework durability: your diligence infrastructure holds up as deal volume scales
- Pipeline velocity: deals move through the process on time with minimal back-and-forth
- Client experience: business owners report smooth, professional interactions with the Investments team
If you want to own an investment function and you are excited about applying rigorous credit thinking to an asset class that has never had it, we want to talk.