Table of Contents
Scaling a startup from $1 million to $10 million in annual recurring revenue is a journey into a new world, especially when your target is the enterprise. The scrappy tactics that secured your first million won't land the six-figure deals needed for the next phase of growth. It requires a fundamental shift in strategy, mindset, and execution. Enterprise sales expert Jen Abel offers a counterintuitive playbook that challenges conventional wisdom, revealing that the path to $10M ARR is less about rigid playbooks and more about creative deal-crafting, visionary storytelling, and building authentic relationships.
Key Takeaways
- Target Tier 1 Logos First: Contrary to popular advice, the biggest names in an industry (like Walmart or Tesla) are often the best early adopters because they are driven to maintain their competitive edge and have the resources to experiment.
- Sell the Vision, Not the Problem: Instead of focusing on specific pain points, effective enterprise selling involves "vision casting"—showing leaders how your solution creates a new opportunity or gives them a competitive "alpha."
- Aim for Six-Figure Deals: Avoid the trap of small $10,000 deals that can give a false sense of product-market fit. Enterprises are accustomed to contracts in the $75,000 to $150,000 range, and a higher price point ensures executive buy-in and commitment.
- Enterprise Sales is an Art: Success isn't about following a script. It’s about creative deal crafting, where every contract is tailored to the customer's unique opportunities and built on a foundation of trust and personal relationships.
- Hire Salespeople Who Can "Cosplay the Founder": Your first enterprise sales hires shouldn't be traditional reps. They need to embody the founder's vision, passion, and creativity to build trust with executive buyers.
Rethinking Your Target Market: Why the "Mid-Market" Doesn't Exist
Many startups get lost in a vaguely defined "mid-market," a strategy Jen Abel argues is a recipe for failure. The sales motions, hiring profiles, and product expectations for small businesses and large enterprises are fundamentally different. Trying to create a hybrid approach means you'll excel at neither. The choice is clear: you're either playing the high-volume, marketing-led small business game or the strategic, sales-led enterprise game.
The Upper SMB vs. Lower Enterprise Trap
When founders say they're targeting the mid-market, they usually mean the lower end of the enterprise. This clarification is critical. If you're selling to a 1,000-person company, you are playing the enterprise game. You need enterprise-grade salespeople, you must command an enterprise-level average contract value (ACV), and you must understand the complex buying processes of large organizations. Blurring these lines leads to hiring the wrong people, pricing incorrectly, and ultimately losing the game before it even starts.
Why You Should Target Tier 1 Logos Immediately
The standard advice is to avoid big-name companies early on, fearing long sales cycles and bureaucracy. Abel’s advice is the exact opposite: go after them from day one. Companies like Walmart, McDonald's, and Nvidia are at the top for a reason—they constantly seek an edge to stay there. They are the true early adopters.
If you can give me just a slight bit of alpha, just a tiny bit... that's where I get promoted.
Landing a Tier 1 logo provides all the validation you need. It attracts investors, top talent, and other customers who want to emulate the industry leader. These companies are willing to take a chance on new technology and often want to help shape a product's roadmap, providing invaluable feedback that can turn a $100,000 deal into a million-dollar partnership.
The Art of the Enterprise Deal: Vision Casting and Strategic Pricing
Closing six-figure deals requires a different kind of conversation. It's not about features and functions; it's about opportunity and transformation. Founders are uniquely positioned for this because they naturally sell the vision, while traditional salespeople are often trained to just solve a stated problem.
Sell the Opportunity, Not the Problem
Problem-selling is tactical and specific. Vision casting is strategic and aspirational. Instead of saying, "We solve X problem," you should be communicating, "Here is where you are today, and here is the superpower we can give you to win tomorrow." This is about selling the outcome—the "Mario on blast," not the mushroom that gets him there. It’s about giving your champion the "alpha" they need to stand out. For example, instead of selling a coding tool by promising productivity gains, you sell it by promising the ability to attract 10x engineers who refuse to work without the best tools.
The Dangers of Discounting and Low ACVs
In the early days, founders often discount heavily to get deals done. This is a critical mistake. The best clients won't nickel-and-dime you; if they do, it's a sign they aren't fully bought into your vision. Pursuing ten $10,000 deals instead of one $100,000 deal can provide a false sense of product-market fit while distracting you with customers who aren't a great match.
Most founders would rather get 10 10k deals than lose nine and get one 100k deal.
Enterprises are accustomed to initial contracts between $75,000 and $150,000. Starting at this level ensures you have executive attention and that the organization is committed to making the implementation successful. A low starting price anchors your value incorrectly and makes future expansion incredibly difficult. It's much harder to justify a 10x price jump from $10k to $100k than it is to grow a $100k deal to $500k.
From Pilot to Partnership: Leveraging Services and Design Partners
Getting your foot in the door of a major enterprise is the first hurdle. How you structure these initial engagements can determine whether you build a scalable product or a custom consulting project. It's a delicate balance between meeting a customer's needs and staying true to your long-term vision.
Use Services as a Wedge
One of the most effective, yet controversial, strategies is to lead with services. Enterprises are experts at buying services—it's often their largest budget item. By packaging your solution as a service, you align with their existing procurement habits. You solve their problem using your technology behind the scenes. Once you've delivered value and built trust, you can transition them to a SaaS model, showing them how they can achieve the same results more efficiently by using the tool themselves. This "do things that don't scale" approach is a powerful way to de-risk the sale for the customer.
Choosing and Managing Design Partners
Design partners are crucial for refining your product, but they come with a risk: they can pull you in the wrong direction. The best design partners are often technology-forward companies that understand the startup journey. The key is to find an internal champion who is genuinely excited about your vision and willing to work with a "janky" early product. However, the founder's job is to filter the feedback. About 80% of what customers ask for is based on old ways of working. The 20% of gold is the insight that refines your vision without derailing it. A founder with a clear point of view knows when to listen and when to say no.
Building Your Enterprise Sales Engine
As you scale past $1M ARR, the founder can no longer be involved in every deal. Building a sales team is the next critical step, but hiring the right people for enterprise sales is notoriously difficult. The profile of a successful early enterprise seller looks very different from a typical sales rep.
Hire Salespeople Who Can "Cosplay the Founder"
Your first hire should not be a VP of Sales from a large corporation, where the brand did most of the heavy lifting. You need someone who can sell the vision with the same passion and creativity as a founder. This might be a former founder, someone with deep product experience, or even an engineer. They must be able to craft unique deals, build genuine relationships with executives, and navigate ambiguity without a playbook. Look for someone who makes you feel confident and excited—ask yourself, "Would I buy from this person?"
The market doesn't want to be sold to. They want to buy.
Given the high failure rate for first sales hires (often 50%), it's wise to hire two people at once to compare performance and increase your odds of success.
A Human-First Approach to Outbound
In an age of AI-powered outreach, the most effective strategy is to be more human. Jen Abel doesn't use automated outbound tools because they all pull from the same databases, hitting the same people with the same generic messages. The real alpha comes from manual, personalized outreach. It's about taking the "back door in," not the front door where everyone else is. This means researching individuals, understanding their context, and sending a short, thoughtful message that feels different. For a $100,000+ deal, spending the time to craft the perfect, authentic outreach is always worth the investment.
The Psychology of a Winning Sale
Enterprise sales is a game of relationships, trust, and creative problem-solving. It's about making your champion look like a hero for bringing you in. This requires a deep understanding of their motivations and a willingness to ask the questions others are afraid to.
Co-Authoring the Deal
A rigid, one-size-fits-all pricing model doesn't work for large deals. The most successful negotiations involve co-authoring the proposal with your champion. Be direct and ask: "This engagement is priced at $150,000. We can adjust the scope to make it bigger or smaller to fit your needs. How do we structure this so that when you go to bat for it, it's an undeniable win?" This collaborative approach builds immense trust and ensures the deal is structured for success within their organization.
The Power of a Quick "No"
Too many salespeople waste months chasing deals that will never close. Getting to "no" quickly is one of the most productive things you can do. If you sense a lack of excitement or poor timing, address it directly. Say, "I'm getting the vibe this might not be a good fit right now. Did I misinterpret that?" This candor is refreshing, saves everyone time, and preserves the relationship for a potential future opportunity. The goal of a first call isn't to get to the next call; it's to determine if there's a real, urgent opportunity. If not, move on.
Conclusion
The journey from $1 million to $10 million in enterprise ARR is paved with strategic choices that defy conventional startup wisdom. It demands that you reject the nebulous mid-market, confidently pursue industry titans from the start, and price your product based on the transformative value you provide. Success lies not in a rigid playbook but in the art of vision casting, the creativity of deal-crafting, and the strength of the relationships you build. By embracing this founder-led, human-centric approach to sales, you can build a powerful engine for growth that not only lands deals but creates lasting partnerships.
