Startup Memo Break #2 — DealStack
Welcome back to my Startup Memo Break series, where I analyze early-stage companies through the lens of a VC. I dive into startups that stand out—not just for their tech but also for their vision, traction, and potential to disrupt. From market dynamics to team strength and product insight, I highlight what makes each startup compelling and where the risk lies.
Founded in 2023, DealStack is an AI-native workflow automation platform for private capital markets. While often bucketed as “fintech,” DealStack is more accurately positioned within legaltech, tackling one of the most fragmented and manual sectors in finance.
As the team puts it:
When there’s no system built for this, you end up with a mess of documents stored in shared drives, Outlook, Excel, and old-school tools that AI can’t help with. That’s the problem we’re solving and the system we’re building.
In April 2025, DealStack raised a $5.5M Seed round, backed by angels from Paul Weiss, Kirkland, Latham & Watkins, KKR, CVC, TA Associates, and Goldman Sachs, signaling strong insider confidence.
Their ambition? To become the operating system for private capital workflows.
🔍 The Problem?
Private capital markets—PE, VC, family offices, secondaries—run on disconnected tools: PDFs, Excel, Word, back-and-forth emails, and lawyers cc’ed in every thread. These workflows are:
Manual
Time-consuming
Expensive
Error-prone
As LP expectations grow and regulation tightens, General Partners (GPs) need to modernize. But existing tools fail to meet the bespoke needs of private markets.
🧠 DealStack’s Solution
DealStack offers a secure, collaborative, and AI-native platform for streamlining deal workflows:
AI-generated and editable NDAs, term sheets, and fund docs
Real-time tracking of legal reviews and deal progress
Built-in audit trails and compliance modules
End-to-end visibility for GPs, LPs, legal counsel, and ops
Supports waterfall calculations, equity tracking, cap tables, and org charts
Importantly, DealStack doesn’t aim to replace law firms and it empowers them by reducing friction and accelerating execution.
They describe themselves as the "workflow layer" rather than a disruptor — a subtle but smart positioning.
🌍 Where DealStack Is Operating
Headquartered in London with a center of excellence in Poland, DealStack’s commercial team operates across Europe and North America. The product is optimized for cross-border transactions, supporting the intricacies of multi-jurisdictional deals, a critical differentiator.
Current GTM targets:
Emerging managers with lean internal ops
GPs managing complex structures
Law firms acting as deal counsel or fund formation partners
🥊 Competitor Landscape
With 13 competitors (5 of them funded), DealStack operates in a growing category. Players like Edda, Bloqhouse, and GlassDollar touch adjacent workflows—but DealStack differentiates through vertical depth.
Its edge lies in:
Purpose-built UI/UX for GPs, LPs, and legal
Strong legal DNA within the founding team
Support for the full deal lifecycle, not just fundraising or IR
This isn’t a generalist tool with capital markets add-ons. It's private capital-first from day one.
🚀 Traction
Despite being early-stage, DealStack is gaining real-world momentum:
Trusted by 30+ private capital firms, including 6 of the top 10 globally
Embedded in workflows representing $2.6T AUM
Clients include Axcel, CVC, Carlyle, Exponent, FSN Capital
Rapid feedback loops from LPs and law firms feeding product development
Their latest round will accelerate AI development and go-to-market scaling. As Lapinski noted:
“We’re releasing our last core model in the coming month and investing heavily in AI. It’s our next layer of depth — but requires the right cornerstones.”
🧑💼 Meet the Founders
Joel Arnell (CEO) – 15+ years in PE law at Kirkland, Linklaters, and Triton. Deep expertise in fund structuring and governance.
Sebastian Lapinski (COO) – Ex-Oaktree and Triton investor with strong operational chops.
Andrew Ho (Co-CTO) – Serial technical founder with 12 years in engineering leadership and multiple exits.
This is a well-rounded founding team with complementary skill sets: legal, capital markets, and product. Beyond the founders, the team brings experience from Amex, Vauban, PwC, Baker McKenzie, Wise, and Virgin Media. They're already supporting clients across 65+ jurisdictions, indicating operational readiness for global scale.
📊 Market Size & Opportunity
Private equity market: $700B+ (2023), expected to hit $1.2T+ by 2032
Workflow automation market: $15B in 2024 → $71B+ by 2031 (CAGR: 23.68%)
New compliance standards (ILPA, AIFMD II) and ESG frameworks are fueling urgency
Even modest penetration into this niche yields large upside. Legaltech for private markets remains wide open.
⏱️ Why Now?
Regulatory pressure and LP demands are accelerating digital transformation
AI is finally able to handle structured + unstructured deal data
GPs are facing cost pressure, looking to do more with leaner teams
DealStack hits the sweet spot between timing, tech maturity, and market readiness.
🚩 Risks & Questions
Scalability across fund types and jurisdictions: Can DealStack’s modular design handle bespoke structures across venture, growth, secondaries, and beyond?
Adoption curve in a high-trust, risk-averse industry: Private capital workflows are sticky not because they’re good, but because they’re familiar. How fast will GPs and legal teams actually switch?
Workflow ownership: Who drives internal adoption (legal, ops, fund managers)? Misalignment here can stall implementation.
Positioning risk: Will this be seen as a must-have operating layer, or a “nice-to-have” automation layer?
AI skepticism: They envision a fully agentic platform handling end-to-end tasks without human intervention. But as someone who wrote their thesis on deal automation, I remain cautious. According to my VC experience and research, hybrid AI-human models outperform in edge-case-heavy environments like early-stage investing.
That said, co-founder Lapinski directly addressed this:
“We provide a deterministic model where the AI always provides the correct answer and can be verified—and customers are really excited about that.”
It’s a bold promise. Whether it holds at scale remains a key watchpoint.
💡 Exit Potential
DealStack sits at the intersection of legaltech, cap table management, and back-office automation, three adjacent markets that are actively consolidating. If they succeed, they’re not just a vertical SaaS solution. They’re infrastructure.
Exit scenarios include:
Strategic acquisition by legaltech incumbents (e.g., Ontra, Litera)
Roll-up target for cap table players expanding downstream (e.g., Carta, Pulley)
Acquisition by large PE firms or LP platforms investing in internal operating systems
Enterprise SaaS giants (e.g., Salesforce, Microsoft) entering capital markets infrastructure
What strengthens their case is not just product-market fit—but strategic relevance. In a world where VCs and PE firms increasingly use automation to improve deal quality, a platform like DealStack doesn’t just streamline it enables smarter, more secure investment decisions.
🧠 My Take as a VC
Private capital has scaled, but its operations haven’t. Behind multi-billion-dollar deals are still fragmented workflows, Excel sheets, and legal bottlenecks. DealStack’s bet is simple but ambitious: bring private equity operations into the AI-native era.
With deep roots in law, PE, and enterprise SaaS, the founding team understands the pain points intimately. Their platform already extends beyond funds to portfolio companies, managing ownership structures, investor onboarding, and compliance. This dual-sided use case increases product stickiness and widens their strategic moat.
If they pull this off, DealStack could become the “Salesforce meets Copilot” for fund operations, standardizing how capital is raised, managed, and reported across jurisdictions.
Would I take the meeting? Absolutely.
Would I lead the next round? Yes.
Why? Because the need for workflow modernization in private capital is no longer optional. It’s existential.
The next generation of fund managers and legal teams won’t tolerate email-based processes and static spreadsheets. They’ll demand infrastructure that enables speed, accuracy, and scale.
And beyond the back-office fix, DealStack represents a shift in how investment decisions are made.
Just as VCs increasingly use automation to evaluate startups more objectively, GPs can use platforms like DealStack to reduce risk, surface red flags earlier, and make smarter, more defensible bets. In an industry where precision matters, that’s powerful.
With solid early traction, a high-trust user base, and a sharp go-to-market motion, DealStack is one of the few vertical SaaS bets in private capital with true breakout potential. One to watch.
📝 If you were an emerging GP or legal partner, would you use DealStack?