AlleyWatch sat down with Thoughtly CoFounder & CEO Torrey Leonard to learn more about the business, its future plans, recent funding round that brings total funding to over $8M, and much, much more…

Who were your investors and how much did you raise?

We closed a $5.5M Seed round, bringing our total funding to over $8M. The round was led by Armory Square Ventures, with participation from nvp capital, Converge, K5 Global, and our returning investors Afore Capital and Greycroft. We’re really proud of the group we’ve assembled — these are investors who understand the nuance of what we’re building and bring genuine strategic value beyond the check.

Tell us about the product or service that Thoughtly offers.

Thoughtly is the AI engagement platform that gives CRMs a voice. We embed AI agents directly into CRM workflows so revenue teams can reach every lead — by call, text, and email — the moment they raise their hand. No engineering lift, no call center infrastructure, no leads going cold. We just launched our full omnichannel platform, so teams can now coordinate voice, SMS, and email from a single system using a no-code builder. It’s designed for go-to-market leaders who need to move fast without pulling in an engineering team.

What inspired the start of Thoughtly?

It started with a pretty clear problem: most revenue teams can only human-touch a fraction of their pipeline. The rest goes cold. Email and SMS drips underperform. And while teams have automated their data workflows and digital channels, phone conversations have stayed largely manual — which creates coverage gaps, slower response times, and missed revenue. We saw AI getting good enough to actually hold real conversations, and thought: there’s an infrastructure layer missing here. CRMs became the system of record for data but never for conversations — and conversations are where deals are actually won and lost. That’s the problem Thoughtly exists to solve.

How is Thoughtly different?

A few things. First, we’re CRM-native — AI agents operate directly inside existing workflows, not as a separate tool teams have to learn and manage. Second, we’re truly omnichannel: one platform coordinating voice, SMS, and email based on CRM data and customer behavior. Third, we’re built for revenue teams, not developers. Unlike legacy CCaaS platforms, IVRs, or voice APIs that require engineering, Thoughtly gets teams live in days. And fourth, the outcomes speak for themselves — our customers are reaching 100% of their pipeline, which is a dramatic improvement over the industry norm of 5–10%.

What market does Thoughtly target and how big is it?

We’re focused on high-velocity, consumer-facing industries where speed-to-lead is everything — education, insurance, mortgage, and real estate. These industries have massive lead volumes, significant revenue per customer, and historically poor conversion rates because follow-up is slow and inconsistent. The conversational AI and GTM automation space is a multi-billion dollar opportunity, and it’s accelerating as revenue teams realize that manual outreach and generic drip campaigns just aren’t keeping up with the pace of modern business.

What’s your business model?

We’re a SaaS platform with usage-based components tied to engagement volume. Customers pay for access to the platform and scale their usage as they grow — which keeps our incentives tightly aligned with theirs. The more leads our customers successfully engage, the more value Thoughtly creates, and the more our business grows.

How are you preparing for a potential economic slowdown?

We’re actually well-positioned here. When budgets tighten, efficiency becomes the priority — and that’s exactly what Thoughtly delivers. We help revenue teams do more with less: reach more leads, have more conversations, and drive more pipeline without adding headcount. The $400,000 in annual headcount savings our customer Nomad achieved is a good example of the ROI that makes Thoughtly defensible even in a tighter environment. We’re also focused on verticals that tend to be resilient — housing, education, insurance. And internally, we’re staying lean and disciplined, deploying capital on things that directly drive customer value.

What was the funding process like?

Fast and focused. We had clear proof to bring to the table — real customers, real outcomes, real numbers. When you can say a customer booked 650 meetings in 90 days or achieved 100% lead coverage for the first time, those conversations move quickly. The investors who moved fastest were the ones who had seen firsthand how broken lead engagement is in our target verticals. We leaned on warm relationships and let the results do the talking.

What are the biggest challenges that you faced while raising capital?

The AI market is genuinely noisy right now, and cutting through that takes work. A lot of companies claim to do AI-powered everything, so demonstrating that Thoughtly is a real product with real enterprise customers getting measurable outcomes required deliberate storytelling. We leaned hard on specifics — named customers, concrete metrics, verifiable proof points — and that’s what built conviction with the right investors.

What factors about your business led your investors to write the check?

A few things: the depth of the problem, the quality of our early customer base, and the speed at which we’ve been executing. Armory Square noted that our ability to accelerate GTM in the industries they’ve backed is unparalleled. nvp capital saw Thoughtly as the infrastructure play to close a billion-dollar blind spot — CRMs have always been the system of record for data but never for conversations. I think our investors also had strong conviction in the team. We move fast, we stay close to customers, and we build things that actually work in production.

A few things: the depth of the problem, the quality of our early customer base, and the speed at which we’ve been executing. Armory Square noted that our ability to accelerate GTM in the industries they’ve backed is unparalleled. nvp capital saw Thoughtly as the infrastructure play to close a billion-dollar blind spot — CRMs have always been the system of record for data but never for conversations. I think our investors also had strong conviction in the team. We move fast, we stay close to customers, and we build things that actually work in production.

What are the milestones you plan to achieve in the next six months?

We just launched our omnichannel platform — call, text, and email in a single CRM-native system — so the next six months are all about scaling that into our core verticals and expanding our customer base. We’re investing in go-to-market infrastructure, deepening integrations with the CRMs our customers already live in, and continuing to build out the team. The north star is simple: make sure every customer we bring on sees undeniable, measurable ROI quickly. If we do that, the rest follows.

What advice can you offer companies in New York that do not have a fresh injection of capital in the bank?

Stay obsessively close to your customers. In a tighter environment, the companies that win are the ones with the strongest customer relationships and the clearest sense of what’s actually working. Don’t raise for the sake of raising — build something people need badly enough that they tell others about it. New York has an incredible ecosystem of operators who’ve been through cycles before; lean on that community. And honestly: do less, better. Focus is a superpower when resources are constrained.

Where do you see the company going now over the near term?

We’re heads-down on omnichannel. The launch of our autonomous CRM platform is a meaningful step — it’s the product our customers have been asking for, and it changes the conversation around what AI engagement can actually do at scale. Near term, we’re going deeper in our core verticals, building out enterprise-grade features, and expanding the team with people who genuinely care about the problem we’re solving. The longer arc is building the system of record for conversational GTM. We think that’s a big company, and we’re just getting started.

What’s your favorite spring destination in and around the city?

Honestly, Chelsea is hard to beat in the spring. My wife Jenna and I have gotten into doing group fitness classes together — there’s something about the neighborhood in April or May, grabbing coffee after a class, the city actually feeling alive again. It’s become a bit of a ritual for us. Highly recommend it over doom-scrolling through a New York winter.

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AlleyWatch sat down with Amperos Health CEO and Cofounder Michal Miernowski to learn more about the business, its future plans, recent $16M funding round that brings total funding to $20.2M, and much, much more…

Who were your investors and how much did you raise?

Amperos Health announced that it closed a $16M Series A funding round, led by Bessemer Venture Partners, with participation from Uncork Capital and Neo.

Tell us about the product or service that Amperos Health offers.

Amperos is healthcare’s first AI-native denial management and revenue recovery solution designed specifically for healthcare providers to combat denials and streamline claims collections for revenue cycle management (RCM) teams. Providers hand off their denied claims, and Amperos handles everything: follow-ups, appeals, calls, paperwork, the works. The AI that Amperos uses works directly within the provider’s existing billing software, acting like a member of their team rather than a separate platform to manage. The result: providers recover more revenue, at lower cost, without hiring more staff.

What inspired the start of Amperos Health?

I spent years as an investor in healthcare services, working with leaders to improve the financial health of their clinics. There, I saw firsthand how the manual, costly burden of billing prevents clinics from growing, serving more patients, and paying their staff competitively. In 2023, I was inspired to found Amperos alongside my cofounders Alvin (CPO) and Wilson (engineering) to bring complementary product and technical depth.

How is Amperos Health different?

Compared to legacy incumbents, our differentiation is that we provide an agentic workforce that can be easily directed to follow a customer’s SOPs, provide auditing on what was worked when, and achieve better outcomes, including high recovery rates at a lower cost.
Our primary differentiator is that Amperos is a true end-to-end platform that can handle a claim from start to finish. Most others in the space only provide a point solution (e.g. AI calling only, appeals only).
Amperos uses AI, which means it works on every claim systematically and comprehensively. A $50 denial gets the same follow-through as a $5,000 one – and providers can see every action in real time. The economics are fundamentally different: AI doesn’t get tired, doesn’t quit, and doesn’t need to be retrained. That’s how Amperos can charge 50% less and recover more.

What market does Amperos Health target and how big is it?

Amperos targets the healthcare RCM market. Right now, American providers are denied $262B of revenue each year from insurance, and spend another $26B trying to recover claims. Even then, only 70% of those claims end up getting paid. And yet, 63% of revenue cycle teams are understaffed, and the role sees 32% annual turnover, leaving major gaps in the workforce.

What’s your business model?

Amperos partners with healthcare providers and integrates directly with their billing systems to provide a highly customized solution for customers. Our subscription pricing model is volume-based, to ensure that our customers achieve ROI regardless of the size of their practice.

How has the business changed since we spoke last June after your seed round?

Our goal has remained the same: lead a new standard in healthcare where providers can navigate RCM with ease. Amperos continues to partner with providers to give more complete, faster information about their claims, which is helping both sides resolve disputes more efficiently — which is good for payers too.

What was the funding process like?

We aimed to run a well-structured process and lined up all materials and potential intros leading up to launch date. As a result, within just a day of launching the raise, we had meetings lined up. We ended up signing our term sheet about 10 days after the fundraising process started.

What are the biggest challenges that you faced while raising capital?

While healthcare RCM has attracted a lot of attention from VC, it is a niche sub-industry. The biggest hurdle was really introducing generalist investors to the space and trying to educate them quickly on how healthcare billing works.

What factors about your business led your investors to write the check?

We’ve seen great traction with investors, driven by the real ROI we drive for customers. That, plus the healthcare and AI experience of our team, led investors to underwrite their investment.

We’ve seen great traction with investors, driven by the real ROI we drive for customers. That, plus the healthcare and AI experience of our team, led investors to underwrite their investment.

What are the milestones you plan to achieve in the next six months?

We aim to rapidly evolve the product and by the end of this year, expand into new parts of the RCM workflow beyond denial management — such as preventing denials and addressing root causes automatically.

What advice can you offer companies in New York that do not have a fresh injection of capital in the bank?

I would say the most important thing is to identify the top 2-3 most important things to make your business successful in the next 6-12 months and focus your time and money in those areas.

Where do you see the company going now over the near term?

RCM today is a manual, constantly shifting domain. New payer rules, new procedures, and constant staff turnover. It’s nearly impossible for any billing leader to stay ahead without AI.
As Amperos expands from denials into other parts of the revenue cycle, the goal is to become the AI-native infrastructure layer between providers and payers. We don’t want to be just automating the work, but continuously optimizing, to make sure providers can maximize reimbursement. We can make this possible by identifying where denials are occurring and making process changes upstream to prevent them in the first place.

What’s your favorite spring destination in and around the city?

On a rainy spring day – the Met! And on a warm day – Prospect Park!

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AlleyWatch sat down with Shade CEO and Co-Founder Brandon Fan to learn more about the business, its future plans, recent funding round, and much, much more…

Who were your investors and how much did you raise?

We raised $14M led by Khosla Ventures and Construct Capital, with participation from Bling Capital. This brings our total funding to $20M. We’re also grateful to our seed investors, General Catalyst, SignalFire, and Contrary, for believing in us early.

Tell us about the product or service that Shade offers.

Shade is the intelligent file system for creative teams. We replace the typical post-production stack with a single unified platform where teams can access, search, review, and archive everything (combines cloud storage like Dropbox, streamable file systems like LucidLink, MAMs like Iconik, review platforms like Frame.io, file transfer services like Signiant, and proxy generation tools).

Post teams get one source of truth for all their media assets, feedback, and approvals, accessible from anywhere.

What inspired the start of Shade?

Emerson Dove (Cofounder and CTO) and I were creatives ourselves and we lived this problem firsthand. We’d spent countless hours shuttling files between five different platforms instead of doing the work we loved. Upload to storage, download to edit locally, export for review, download revisions, repeat.

We started having hundreds of conversations with editors and heads of post and kept hearing the same frustration. This wasn’t unique to us. Teams everywhere were spending more time managing files than creating. That’s why we started Shade in 2024: to build a single source of truth for media teams.

How is Shade different?

The rest of the industry forces teams to choose between cloud collaboration and real-time performance. Legacy tools either make you download entire files before you can work with them, or they solve one slice of the workflow and leave the other four to a different vendor.

Shade is the only platform that unifies storage, streaming, AI-powered search, review, and archive in one place. Our block-level streaming engine makes a 100GB file editable the second it uploads, as if it were stored locally. Our AI processes footage on ingest, so teams can search by what’s actually in the video, not just what someone remembered to tag.

Everyone’s building the AI brain. We’re building the memory system that makes it work.

What market does Shade target and how big is it?

Shade targets creative and post-production teams across film, TV, advertising, sports, gaming, and enterprise video. But there are no real industry limits here. Any team working with large media files runs into the same infrastructure problem, which makes this a multi-billion dollar opportunity across storage, collaboration, asset management, and review.

Today, the average production team juggles five or more disconnected platforms and loses 30+ hours per project moving files between storage, editing tools, and review. Feedback scatters across Frame.io, email, and Slack. Finding a specific clip in a multi-terabyte library means scrubbing through hours of footage because traditional storage can’t search what’s inside the files.

Shade consolidates the entire workflow into one platform. Editors mount Shade as a cloud-native drive and stream files directly into their NLE without downloads. AI automatically tags and transcribes on ingest, so teams can search by what’s actually in the video. Review happens in-platform with comments syncing directly to NLE timelines.

What’s your business model?

We charge per seat and per terabyte of storage, with two ways to buy: self-serve and enterprise.

Self-serve is designed for smaller teams who want to sign up on the website, start a trial, and manage their own subscriptions. Enterprise is sales-led and uses a bucketed package approach for larger teams, with volume discounts on both seats and storage. Enterprise plans include SSO/SAML, SCIM, session watermarking, audit logging, and DRM.

How are you preparing for a potential economic slowdown?

The best defense in any market is solving a real, painful problem that customers can quantify. Every Shade customer can point to hours saved per project and headcount freed up. When budgets tighten, tools that consolidate four or five line items into one become even more valuable, not less. We’ve built the business around that.

What was the funding process like?

We spent time meeting a lot of investors and looking for partners who understood both the creative industry and where AI infrastructure is headed. Khosla and Construct saw it quickly, and the process moved fast from there.

What are the biggest challenges that you faced while raising capital?

The hardest part was helping investors outside of post-production understand just how broken the current workflow is. Most people don’t realize that creative teams are losing 30+ hours per project to file management, or that the average team is paying for five separate tools to do what should be one. Once we walked them through the day-to-day reality, the conversation changed.

What factors about your business led your investors to write the check?

The size and urgency of the market need. Post-production is shifting from hard drives to the cloud right now, and the fragmentation that shift has created is measurable in hours and dollars per project. Investors saw a real, unmet problem, a product already used by teams at the scale we’re targeting, and a clear path to becoming the file system of record for creative work.

What are the milestones you plan to achieve in the next six months?

Four things we’re focused on:

Building a file system people love to use. If Shade is the tool all data flows through, it needs to be a place teams love to work in every day. We’re pouring resources into a unified design system, better interactions, and a beautiful user experience.

Building the smartest search engine for any modality. We’re going beyond semantic search with custom metadata and doubling down on search across images, video, and text, with direct moment detection and time-specific metadata. We’re also investing in how AI can sort, organize, and label automatically.

A file system that represents your business. Most file systems just store files, or just do review, or just act as a MAM. We want Shade to represent your actual business (events, sports teams, clients, projects) and let you build no-code workflows that automate the busywork. We’re not just building a system of record. We’re building a system of action.

The most extensible file system. For workflows to be truly connected, Shade needs to be extensible. We’re doubling down on developer experience, and our Shade App Store is coming

What advice can you offer companies in New York that do not have a fresh injection of capital in the bank?

Be product-led. Capital amplifies what’s working, but it doesn’t create it. The companies that end up raising from a position of strength are the ones whose customers are already telling their friends. Focus every ounce of energy on making something a specific group of people genuinely can’t live without. Revenue and word of mouth will follow, and so will investors.

Where do you see the company going now over the near term?

Over the next six to twelve months, we’re focused on making Shade the operating layer for creative work, not just a place files live. That means shipping Custom Objects and Automations so teams can model their actual business (events, sports teams, clients, projects) inside Shade and automate the busywork around ingest, review, and delivery. It also means deepening our integrations across the tools post teams already use, so Shade becomes the connective tissue between creative, production, and delivery.

What’s your favorite spring destination in and around the city?

The East Village. Our office is there, and that’s where the energy is in New York!

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AlleyWatch sat down with Rohit Bhadange, CEO and Founder of Zamp, to learn more about the business, its future plans, recent funding round, and much, much more…

Who were your investors and how much did you raise?  

The company has raised $30M in total funding to take sales tax off finance teams’ plate. Our latest round was led by Acrew Capital with participation from Thomson Reuters Ventures, along with several of our accounting firm partners who invested directly. We’re also backed by 20Growth, Friends & Family Capital, Good Friends Venture Capital, and other strategic investors from earlier rounds.

Tell us about the product or service that Zamp offers.

Zamp is the operating system of sales tax with a built-in managed service. We combine AI agents with tax and legal professionals to own the entire sales tax compliance lifecycle: filing, registration, notices, data normalization, and taxability mapping. Unlike other vendors, we own the outcome. If we get it wrong, we cover the penalty. 120+ accounting firms use Zamp to deliver managed sales tax compliance to their clients — as a referral partner or white-label service.

What inspired the start of Zamp?

I spent the first part of my career on the investing side in private equity, growth, and early-stage venture across a few industries. The one thing that kept coming up was sales tax. Finance leaders were constantly complaining that nobody was helping them. Every year they’d have this liability on the balance sheet they couldn’t predict. Nobody was owning the outcome with them. They’d buy the software and still have to figure it out themselves, or hire a third party who’d manually piece it together across jurisdictions to maybe get it right with zero visibility. Sales tax was a black box. I started Zamp with a few other industry operators to fix that.

How is Zamp different?

Three things. First, we built our own tax data layer across thousands of jurisdictions globally, instead of relying on third-party data. Second, we own every workflow end-to-end: filing, registration, notices, data normalization, taxability. Third, we pair AI agents with tax and legal professionals to deliver the best outcome for the customer. Service matters to us. We think about what’s right for each customer and meet them where they are. And we stand behind it — if Zamp gets it wrong, Zamp covers the penalty. That’s only possible because we control the data, the workflows, and the execution.

What market does Zamp target and how big is it?

Global sales tax compliance is $30B+ market — 12,000+ jurisdictions in the U.S. alone and dozens of countries globally. We serve e-commerce, SaaS, digital services, retail, and increasingly accounting firms that deliver compliance to their clients. The accounting firm channel (~$20B) is particularly important because 75% of U.S. accountants are expected to retire in the next 15 years, and firms can’t hire their way through it. Zamp is how they scale their sales tax practice without building a dedicated team.

What’s your business model?

We charge an annual fee to own the entire sales tax lifecycle based on the complexity of the business. If we get it wrong, we cover the penalty. That’s different from legacy or other newer providers who charge per filing, per registration, or on basis points. They charge for inputs. We charge for outcomes.

How are you preparing for a potential economic slowdown?

The business was built to be efficient. Our agents and our product are the leverage — not headcount. We don’t need to hire 50 more people to support 50 more firms. That’s why our margins in this business are the best in this space. Combined with over 95% client retention and 98% partner retention, the business model is resilient regardless of macro.

What was the funding process like?

Tight. We weren’t actively raising; we were focused on building the right product and delivering for our customers. Word got around, we were getting preempted by several firms, and the round came together quickly with a small group we wanted to work with.

What are the biggest challenges that you faced while raising capital?

Deciding who to work with. We had more demand than we needed, so the hard part was saying no to great firms to keep the cap table focused.

What factors about your business led your investors to write the check?

Three things. First, our customers did most of the work; over 95% client retention, 98% partner retention. When your customers are speaking for you, there’s not much left to explain. Second, the infrastructure approach combined with real unit economics. We built our own data layer, own every workflow end-to-end, and it shows in the numbers; one person on our compliance team is now doing what used to take 12. Third, the distribution model. 120+ accounting firms already on the platform is a very different motion than selling direct to individual companies, one at a time.

Three things. First, our customers did most of the work; over 95% client retention, 98% partner retention. When your customers are speaking for you, there’s not much left to explain. Second, the infrastructure approach combined with real unit economics. We built our own data layer, own every workflow end-to-end, and it shows in the numbers; one person on our compliance team is now doing what used to take 12. Third, the distribution model. 120+ accounting firms already on the platform is a very different motion than selling direct to individual companies, one at a time.

What are the milestones you plan to achieve in the next six months?

Scale the accounting firm channel with our partnership program (Referral and White-Label), expand AI agent coverage across more service layers like, and continue building compliance depth by country and vertical. Clear concrete target: increase one person’s output from 12x to 100x.

What advice can you offer companies in New York that do not have a fresh injection of capital in the bank?

Capital efficiency is the advantage when capital is tight. Build a great product that creates leverage, not one that requires more headcount. If your only path to scale is adding people, the math won’t work to keep the business alive. Focus on retention over new logos. Great companies compound on customers who stay. And stand behind your work. Customers can tell the difference between a tool and a partner.

Where do you see the company going now over the near term?

We’re scaling the operating system. More firms, more countries, more service layers, deeper agents, smarter automation. The goal is to be the category leader for sales tax globally, and to enable every accounting firm to deliver sales tax compliance at scale without hiring.

What’s your favorite spring destination in and around the city?

Post-tax-season tennis. April 15 comes and goes, the courts finally thaw out, and the whole city gets back outside. Central Park, Riverside Park, or when I can get out to Queens, the Billie Jean King National Tennis Center, home of the US Open. That’s spring to me.

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