Matt Wiseman

Thrilled to announce that Together Fund is investing in Sentra, alongside a16z speedrun! You track results in Jira. Decisions in Notion. Conversations in Slack. But the reasoning, the debates, trade-offs, and context behind why you chose A over B, disappears into what we call "Dark Matter." A decision made in March looks insane by July because no one remembers the constraints that made it smart. I lived this firsthand at Twitter scaling from 800 to 8,000 employees, and at Google while launching AI Overviews to billions at planet scale. The problem isn't process. Process is compensation for something deeper: organizational amnesia. An organization’s "Systems of Record" doesn’t solve this, they encode it. They store what happened, never why. That's why we are investing in Sentra. Sentra is the always-on collective memory that eliminates organizational amnesia by maintaining accurate context for all members and agents, functioning as an operational nervous system. It connects to every channel where work happens, meetings, Slack, email, code commits, docs, calendars, and treats them not as artifacts to search, but as living signals to synthesize. The fleeting and the permanent, unified into a memory that understands. The founding team is built for this: - Jae Gwan Park (CEO): Product-first founder, memory systems research at UofT and MIT - Ashwin Gopinath (CSO): Former MIT professor, created "Reflexion" (NeurIPS 2023), agents that learn from mistakes, 2x founder - Andrey Starenky (CTO): Early Vapi engineer, ex-IBM, built to process enterprise-scale data firehose Together is an operator-led fund. We invest in problems we've lived. This is one of them. Many congrats Jae, Ashwin and Andrey, we are so excited to partner with you! Read the full thesis: https://lnkd.in/gixj9cE4 Book a demo: https://www.sentra.app/ #OrganizationalMemory #AI #Sentra #TogetherFund #a16z #ContextGraphs

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Dayna Grayson is a leading VC who has “sat in every chair” at a young age. She founded Construct Capital with Rachel Holt, an early leader at Uber. Together, they are tackling the digitization of industry. Dayna will discuss macro trends, what it takes to be a founder, and the potential for AI. She is one of the few who have successfully blended a career of operations and investing.  Check out our discussion at: https://lnkd.in/eYBUGjbW #leadershipdevelopment

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The hottest role in AI startups right now isn’t Forward Deployed Engineers. It isn't GTM Engineers. It’s Deployment Strategists. Decagon calls it an “Agent Product Manager.” Harvey calls it a “Solutions Architect.” Palantir Technologies has had versions of this role for years. And the salaries are climbing fast: - Decagon: $200k–$285k - Palantir Technologies: $120k–$200k - Figma: $150k–$260k - Ramp: $100k–$180k - Harvey: $190k–$260k So who are these people? They are usually pseudo-technical -- CS or engineering majors, or folks with technical work experience. Many come from 2 years in consulting, IB, or PE, then jump into startups to get their hands dirty. They are young, hungry, polished, and comfortable being in front of customers. What do they actually do? They make sure enterprise AI deployments succeed. A $100k+ deal does not survive on a nice pitch or a self-serve onboarding flow. It survives if the customer sees value in the pilot. That means: - Embedding directly with the customer - Designing prompt logic for specific workflows - Working with engineering to align integrations and data flow - Helping exec teams define their AI roadmap - Running feedback loops into product and GTM Why does this role matter so much? Because enterprise AI is messy. Integrations, data transfer, and adoption make or break a deal. Most buyers are using AI for the first time, and each has unique workflows. Deployment Strategists bridge that gap. They own the outcome. They are accountable for making pilots successful, which often means millions in revenue down the line. At Conversion, Sam Bochner has been leading this work for us. We are now thinking about scaling it into a full team. Because a few successful pilots can fund an entire department, and the cost of failed deployments is too high to ignore. Is this just a rebrand of customer success? Not really. Success is about answering tickets and renewals. Deployment Strategy is about going deep with a few enterprise accounts, extracting maximum value, and ensuring the pilot closes into a multi-year contract. Call it Agent PM, Solutions Architect, or Deployment Strategist. Whatever the title, this is becoming one of the most important roles in AI SaaS.

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The Headline family is experiencing incredible momentum, and today our portfolio company DeepIP is announcing a $25M Series B, bringing total funding to $40M.  This is the kind of company that doesn’t just add AI to a workflow, but it sets the standard for an entire category. The momentum speaks for itself: 1️⃣ 10x ARR growth in < 18 months 2️⃣ Trusted by 400+ law firms and leading corporate IP teams globally 3️⃣ 2M+ chats on the DeepIP platform We’ve had the chance to back FX (Francois-Xavier) L. and Edouard D., leading their Seed round with Headline. Watching them take on a problem as complex and high-stakes as patent work has been genuinely impressive. And working with them has been an absolute pleasure: these 2 are coupling very high ambition and humility. Tech built in Europe, but opening the US office very early and FX starting a life in NYC with his family with 0 hesitation in order to build a global category leader in the IP industry. What convinced me early is still what stands out today: patent teams don’t need another standalone AI tool. They need something that fits the way the work actually happens: documents, long-running matters, multiple stakeholders, and zero room for sloppy context handoffs. Big congrats to the whole DeepIP team + Korelya Capital, Balderton & Serena Proud that we’re doubling down at Headline and continuing the support for what’s next!

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I’m thrilled to officially announce our $3M seed investment in Propel People, a company we built inside the 1848 Ventures studio to tackle one of the biggest challenges facing the #construction industry today: the skilled #labor shortage. For small and medium-sized contractors, hiring isn't just a challenge. It's the number one threat to their growth, profitability, and safety. With 94% of contractors struggling to find qualified workers, it’s clear that traditional hiring methods aren't built for the trades. That’s why we built Propel People. It’s a mobile-first, AI-powered hiring platform designed for how construction actually works: in the field. By leveraging smart candidate ranking, instant #SMS-based screening, and a fully #bilingual interface, Propel helps contractors build great crews faster and more efficiently. I’m also thrilled to formally announce that industry veteran Dexter Bachelder is at the helm as CEO. Having worked with Dexter and the team over the last few months, we've already seen the impact of his leadership. His 25 years of experience scaling construction tech companies will be instrumental as Propel People enters this initial stage of growth. This investment reinforces our core thesis at 1848 Ventures: building AI-native companies that solve fundamental pain points for the #SMBs that form the backbone of our economy. A huge congratulations to Dexter and the entire Propel People team on this milestone. We are incredibly proud to partner with you to support the people who build our world. Read the full announcement below. #constructiontech #venturecapital #seedfunding #ai #skilledtrades #smb

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In an ecosystem flooded with service-first startups chasing scale through funding, Urban Company stands out by doing the hard (and right) thing—building a real business. Their recent shift from being a pure-play service marketplace to developing tangible, monetizable products is a playbook more entrepreneurs should study. Too many service startups stop at aggregation—thinking scale alone will drive defensibility. Urban Company went a step further: ✅ Leveraging deep consumer insights ✅ Creating integrated solutions ✅ Building new revenue lines rooted in real-world usage This is what scaling with purpose looks like. Instead of chasing round after round of capital to keep the engine running, they’re creating sustainable value by aligning product innovation with the trust and access they’ve already earned through services. For founders building in services: 💡 Don’t just deliver the service. Understand the gaps around it. Own the value chain. Monetize where others overlook. Urban Company is showing what it means to evolve with intent. A solid reminder that great businesses aren’t built on burn—they’re built on depth. #Entrepreneurship #Startups #Innovation #BusinessStrategy #ServiceBusiness https://lnkd.in/dzNHtpBS

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Every hire, product feature, and GTM experiment is a capital allocation decision, most teams just don’t call it that. I’m kicking off a 3-part series on capital allocation for founders, operators, and finance leaders with a simple question: ➡️ Will the next $1 you deploy become worth more than $1? Series overview Part 1: defines the core concept + the math Part 2: where capital goes + how to measure whether it’s working Part 3: AIMS framework for communicating allocation decisions to management teams and your board Part 1 (attached here) lays the practical foundation: 🔹 The $1 invested test and ROIIC vs. hurdle rates (scoreboard vs. decision lens) 🔹 A lightweight “investment brief” to evaluate bets (GROW / BUILD / BUY) 🔹 The small metric toolkit that translates finance into operating decisions (NPV / payback / ROIIC / incremental margin) 🔹 Early-stage proxies when DCF inputs are unknowable (burn multiple + revenue quality) 🔹 Operator “vital signs” to spot drift early (profit engine, leverage, cash conversion, optics) Series Roadmap ✔️ This series (Parts 1–3): breadth-first. shared, lightweight framework to define value creation, choose decision-grade metrics, and communicate tradeoffs clearly ✔️ Next series: depth-first. momentum drivers + operational decisions that need near real-time measurement to spot drift early and course-correct fast Read Part 1 here and Part 2 and 3 on substack. Next Series will be out next week. 💰 What’s one bet you’re funding right now, and how will you prove it’s working?

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