The AI revolution is creating an explosion of disruptive technology companies. Many can build truly revolutionary products. Few have the knowledge, expertise, and infrastructure to go to market at scale. That's where S2 Ventures comes in.
AI has collapsed the time and cost of building transformative technology. Founding teams can ship products in weeks that once took years. But the hardest part of building a company hasn't changed: turning a great product into predictable, scalable revenue.
That requires sales infrastructure, GTM playbooks, buyer networks, and operator-level expertise that most startups don't have — and can't hire fast enough.
"We don't write checks and wait. We deploy a full go-to-market engine — and we've already built one."
For the right company, we invest more than capital. We deploy an entire go-to-market infrastructure — sales teams, technology stacks, buyer networks, and operating playbooks — for equity.
You've built something revolutionary. Now you need a revenue engine that matches it.
We invest scalable go-to-market capability — not just capital — for equity in select technology companies. Our portfolio companies provide the sales infrastructure, technology stacks, and buyer networks that most startups would take years to build on their own.
You know something in your go-to-market is off, but you can't pinpoint what.
We diagnose the gaps in your sales process, market positioning, and revenue operations. Then we fix them. Not with a 90-page deck. With hands-on execution alongside your team.
A transaction is coming and you're not sure you're ready for it.
We guide technology companies through acquisitions, divestitures, and funding events. We've been on both sides of the table and we know what buyers look for — because we've been the buyer.
They pair breakthrough technology with battle-tested go-to-market execution. They don't just build — they ship, sell, and scale. They find partners who bring buyer networks, revenue playbooks, and operator instincts. They compound faster, raise at better terms, and exit with more leverage.
They build brilliant products and wait for the market to come to them. They hire the wrong VP of Sales. They take capital from investors who can't help them operationally. They burn runway on go-to-market experiments that an operator could have diagnosed in a week. The window closes.
If you've built something disruptive and you need a go-to-market engine that matches it — not someday, but now — we should talk.
Start a ConversationMost venture investors write checks and offer introductions. Most consultants deliver slide decks and leave. S2 Ventures is neither. We're an operator-led investment firm that deploys a fully built go-to-market infrastructure — sales teams, revenue technology, buyer networks, and battle-tested playbooks — into the companies we back.
We built it. We own it. And for the right company, we invest it for equity.
Steve Schilling founded S2 Ventures in 2011 after nearly two decades on the operating side of technology companies. Not as an advisor. As the person responsible for the P&L.
At Cypress Communications, he led a turnaround as President & CEO: reduced costs by $8 million annually, grew VoIP revenues by 280%, and guided the company to a successful sale to Broadvox.
At Convergent Media Systems, he transformed a hardware-dependent digital signage company into a recurring-revenue DSaaS business, generating $30M+ in new recurring revenue with 50%+ gross margins, leading to acquisition by Sage Networks.
Today, Steve has assembled a portfolio of companies that together form a complete go-to-market engine — from sales strategy and lead generation to revenue technology and AI-powered market intelligence. That's not a consulting offering. That's infrastructure.
Managing Partner, S2 Ventures
Over 25+ years, Steve has served as CEO, President, and CRO of B2B technology companies. He has led turnarounds, built sales organizations that generated hundreds of millions in pipeline, and guided multiple companies through successful exits.
Active memberships:
Three steps. No wasted motion.
We start by understanding your business the way an operator would. Revenue model, sales process, competitive position, team capability, and market timing. No intake questionnaire. A working session.
Most companies try to fix everything at once and fix nothing. We identify the two or three levers that will move the business fastest and concentrate all effort there.
We don't hand off a plan. We deploy our portfolio's GTM infrastructure directly into your business — the sales teams, the technology, the playbooks, the buyer networks. That's the S2 difference.
S2 Ventures, LLC is an operator-led investment and advisory firm based in Atlanta, GA. The firm invests scalable go-to-market infrastructure for equity in disruptive B2B technology companies. S2 Ventures is the parent entity of Growth Orbit, Sales Tech Partners, TechSignal, RagingWine, Sales Symphony, RevOps-as-a-Service, and other portfolio companies.
View Our PortfolioAI has made it possible to build transformative products faster than ever. But scaling revenue still requires the same things it always has: strategy, process, infrastructure, and operator expertise. We bring all four.
For select technology companies where our portfolio's infrastructure creates disproportionate value. We are highly selective — but for the right fit, we invest our full GTM capability for equity.
For companies that aren't the right fit for equity investment but need operator-level expertise to fix their revenue engine.
Your pipeline is inconsistent. Your close rates are declining. Your sales team is busy but not productive. We redesign the sales process, restructure the team, fix compensation models, and build pipeline development systems that produce repeatable results.
You're selling to everyone and closing no one. We define your ideal customer profile, sharpen your positioning, and build a channel strategy that concentrates effort where it converts.
Your margins are thin and your operations don't scale. We find the inefficiencies, fix the cost structure, and prepare the business for its next stage — whether that's a growth round or an exit.
A transaction is on the horizon and you're not positioned for maximum value. We handle buy-side and sell-side advisory: positioning, valuation preparation, due diligence support, and deal execution.
You need an experienced CRO, President, or CEO but you're not ready for a full-time hire. We step in as interim executives during transitions, bringing immediate operating capability without the 6-month learning curve.
It means we invest our go-to-market infrastructure — sales teams, technology, playbooks, buyer networks — directly into your company in exchange for equity. Instead of raising capital and spending months building a sales org from scratch, you get a proven revenue engine deployed on day one.
Very. We invest our portfolio's full infrastructure — people, technology, networks — so we only take on companies where we're confident the GTM capability we bring will create outsized value. The fit has to be right for both sides.
That's fine. We also provide pure advisory — sales transformation, GTM strategy, M&A guidance, and fractional leadership. Investment is one model. Operating expertise is the constant.
B2B technology companies — particularly AI-driven and SaaS companies — that have product-market fit but haven't cracked scalable revenue. If you've built something the market needs but you can't get it to market at scale, you're exactly who we're looking for.
Each S2 Ventures portfolio company represents a piece of the go-to-market machine. Together, they form a complete infrastructure that can be deployed into the companies we invest in — from strategy and pipeline generation to revenue technology and market intelligence.
Sales Transformation & Pipeline Generation
The engine room. Growth Orbit provides B2B sales consulting, lead generation, and fractional sales leadership. HubSpot Gold Partner. From strategy through execution — sales transformation that produces predictable, repeatable revenue.
growthorbit.comAI-Native Revenue Technology
The tech stack. Sales Tech Partners rebuilds revenue technology for B2B companies — CRM optimization, AI tool integration, and revenue operations alignment. Strategy before technology. Results in 90 days.
salestechpartners.comAI-Powered Market Intelligence
The radar. TechSignal is an AI-powered platform that surfaces real-time buyer signals, competitive intelligence, and market opportunities. Know who's buying, what they need, and when to engage — before your competition does.
techsignal.newsWine Discovery & Review Platform
The proof of concept. RagingWine is a content-driven discovery platform that rates restaurant wine programs with honest, opinionated reviews and real metrics. A showcase for the S2 content-to-commerce playbook and AI-powered content at scale.
ragingwine.comOrchestrated Sales Performance
The performance engine. Sales Symphony fixes B2B sales teams that are missing quota by building a defined sales process, compelling messaging aligned to buyer journeys, and effective coaching for managers and reps. Audits, playbooks, hiring frameworks, and skills workshops — turning ad-hoc selling into consistent, repeatable revenue growth.
salessymphony.comRevenue Operations Intelligence
The intelligence layer. ROaaS gives B2B companies a real-time view of their total addressable market — measuring how much of it lives in their CRM, how well it's covered, and where the gaps are. TAM coverage scoring, Salesforce data quality analysis, and engagement analytics, delivered as a managed service.
roaas.aiWhen S2 Ventures invests in a company, we don't introduce you to vendors. We deploy our own portfolio's capabilities directly into your business. Sales teams. Technology. Intelligence. Networks. On day one.
Talk to Us About InvestmentNot thought leadership for thought leadership's sake. Every post teaches one thing you can use immediately. Full articles coming soon.
The B2B sales landscape is shifting beneath everyone's feet. Companies that don't adapt their sales models to leverage AI will find themselves with expensive teams producing diminishing returns.
Coming SoonBefore you sign with a lead gen vendor, understand what actually works, what's a waste of money, and what questions most companies forget to ask.
Coming SoonThe most important lessons from building companies aren't about revenue or exits. They're about the principles that make everything else work.
Coming SoonWhy the explosion of AI-built products is creating an unprecedented demand for go-to-market infrastructure.
What most companies get wrong about sales process, team structure, and pipeline development.
Candid takes on decisions founders face. Written from the operator's chair, not the advisor's podium.
What buyers actually look for, how to prepare, and the mistakes that destroy value.
Whether you've built something disruptive and need a GTM engine, you're preparing for a transaction, or you need operator-level advisory — we'd welcome the conversation. No pitch required. Tell us what you're working on.
Why S2 Ventures
Most investors write a check and wait. We deploy an entire go-to-market machine.
Most consultants give you a deck and leave. We built the infrastructure and we run it with you.