
The firm
Strategy and engineering, on the same team.
21 Arrows Ventures helps companies turn ambitious ideas into real-world growth. We work on the problems that don't fit a single discipline — where the strategy, the product, and the technology all have to move together — and we stay accountable to what changes in the business, not what ships.
Capabilities
One firm, the whole arc.
- AI integration & agents
- Custom software & platforms
- Digital experience & web
- Systems integration & automation
- Search, content & demand
- Venture design & spinouts
Partners leading every engagement
Typical time to first working release
Layers between strategy and build

How we run
Four commitments we don't negotiate.
Strategy is the first deliverable.
Before anything is built, the business case is written down: the constraint, the value at stake, and the arithmetic that says this is worth doing.
Senior people, small teams.
Engagements are staffed thin and senior. Fewer clients, deeper work, no layer between the thinking and the building.
Numbers or nothing.
Every engagement carries a target — hours recovered, errors removed, revenue booked — and is reviewed against it on a set cadence.
Product discipline throughout.
The firm builds and operates its own companies. Client work runs on the same standards our own ventures are held to.
VenturesLeadership
Kyle Jacobsen
Partner, Operations & Strategy
Kyle has over 25 years of technical and operational experience, including a decade of hands-on management of a multi-specialty healthcare group.
He has a distinguished history of designing and implementing workflows that dramatically increase both productivity and revenue — turning operational friction into measurable margin.
His background spans IT infrastructure management, accounting, and healthcare operations, complemented by Lean/Six Sigma training and leadership roles in the Medical Group Management Association (MGMA). He understands exactly where a process breaks down and how to fix it.
- Practice Management
- Lean/Six Sigma
- MGMA Leadership
- Revenue Optimization
Matt Young
Partner, Technology
Matt is an experienced technology executive with a proven track record of building and scaling platforms. As CTO and later COO of HelloHero, he developed the core IT infrastructure powering PT, OT, SLP, and mental health services across over 100 schools in 30 states.
At HelloHero he built the referral systems, automated scheduling tools, and compliance reporting that service managers relied on daily, before moving into the COO role overseeing a team of roughly 400 employees and operations.
With a Computer Science degree from Binghamton University and deep expertise across the full stack — cloud infrastructure, AI/ML, mobile, and enterprise integrations — Matt brings the technical vision to every engagement.
Work behind the name
- Platform Architecture
- AI/ML
- Operations Leadership
- Cloud Infrastructure
Daniel O'Sullivan
Partner, Product
Daniel brings over a decade of senior product and UX leadership in regulated, high-stakes enterprise software — banking, retail, and healthcare. He owns product strategy, roadmap, and user experience, translating operational complexity into software people will actually adopt and use.
He concurrently serves as Chief Product Officer of Crave Retail, leading a fitting-room intelligence platform used by some of the world's largest retail brands. Earlier he led UX strategy at nCino from startup through its public offering, shaping software that runs inside many of the world's largest financial institutions.
Daniel is the creator of UX Distilling, a design methodology that has gone globally viral, and a repeat Dreamforce speaker and IBM conference keynoter. He coaches executives, advises founders on product direction, and serves as Vice President of eMYRge, the technology nonprofit anchoring startup growth across coastal South Carolina.
Work behind the name
+ dozens more
- Product Strategy
- UX Leadership
- Regulated Enterprise SaaS
- Executive Coaching
Where we work
The firm is based in Myrtle Beach, South Carolina, serving the Grand Strand — and delivering remotely for clients nationwide. The businesses here, from medical groups to construction to hospitality, are exactly the operations where modern software pays back fastest.
Start a project
Bring us the hard one.
A 30-minute conversation about the constraint you're working around. No pitch deck required.











