If you’re stuck doing all the selling yourself, here’s the reality: scaling from $2M to $10M ARR requires a team. Founder-led sales may have worked initially, but it won’t scale. To hit $10M ARR, you’ll need:
- 100 customers with an average contract value (ACV) of $100K.
- 25 new deals annually to offset a 25% churn rate.
- A team to close 2 deals per month per rep while maintaining a strong pipeline.
This shift involves documenting your sales process, hiring the right first sales rep, and leveraging tools like AI to systematize and scale. Here’s how to transition from founder-led to team-led sales without stalling growth.
The Math: How Many Deals and Reps You Need to Hit $10M
The Math Behind Scaling to $10M ARR: Deals, Reps, and Pipeline Metrics
Turning ARR Goals Into Deal and Pipeline Targets
Let’s break down what it takes to hit that $10M ARR milestone.
Starting with a $10M ARR goal and assuming an average contract value of $100K, you’ll need 100 active customers. But here’s the catch: with a typical 25% annual churn rate for B2B SaaS companies, you’ll lose about 25 customers each year. To maintain your ARR, you’ll need to close 25 deals annually – and even more if you’re aiming for growth.
This boils down to closing 2 deals per month across your team. If your demo-to-deal conversion rate is around 25% (a common industry standard), you’ll need to run 8 demos every month to hit those 2 deals. Now, if about 20% of your leads convert into demos, that means generating 40 qualified leads monthly becomes your target.
Here’s another factor to consider: a sales rep typically manages 50–100 qualified leads per month. For lower-value deals (around $50K) with shorter sales cycles of 30–45 days, top reps might close 3–4 deals per month. On the other hand, with higher-value deals ($100K) and longer sales cycles, you can expect fully ramped reps to close 2–3 deals monthly.
With these numbers in mind, it’s clear that scaling beyond founder-led sales is essential to meet these goals.
Scaling Beyond Founder-Led Sales
The math makes one thing obvious: you can’t do this alone. While founders often drive early sales, hitting $10M ARR requires a team effort.
Adding Account Executives (AEs) not only increases your ability to close deals but also gives you more time to focus on strategy and long-term growth. Keep in mind, though, that new reps typically need 2–4 months to ramp up before they hit their stride. So, your first sales hire might take a while to make a noticeable impact on revenue.
When to Grow Your Sales Team
Timing is everything when it comes to expanding your sales team. Once your sales pipeline starts to exceed what you can handle alone, it’s time to make your first hire.
Early on, when you’ve validated your sales process and gained some traction, bringing in your first AE is a smart move. Look for someone who can wear two hats: a player-coach who can close deals while helping you refine and document your sales strategies. Avoid jumping the gun and hiring a VP of Sales too soon – they’re better suited for scaling established systems, not building them from scratch.
As prospecting starts eating up more of your time, consider adding another AE and a dedicated Sales Development Representative (SDR) to focus on lead generation. This allows you to shift your focus from closing every deal yourself to building a reliable, scalable sales pipeline. Over time, you might promote a standout AE into a managerial role to guide new hires. And when your team grows large enough to require more structure and leadership, that’s when bringing in a VP of Sales makes sense to keep the momentum going.
Document Your Sales Process Before You Hire Anyone
Many founders make the mistake of hiring sales reps without having a clear, repeatable process in place. You might have closed deals relying on your instincts, personal relationships, or the product knowledge that lives in your head. But without proper documentation, these valuable insights can’t be passed on to others.
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Before you bring in a new sales hire, dedicate 30–60 days to documenting your sales approach. This groundwork ensures that your proven strategies become a teachable system. It also gives you the foundation to create a concise playbook for your team.
Record and Analyze Your Last 20 Sales Calls
Start by gathering recordings of your last 20 sales calls. If you haven’t been recording, now’s the time to start. Use tools like Zoom’s built-in recording feature or platforms like Gong or Chorus to capture these conversations. A solid dataset will help you uncover patterns.
Listen closely to these calls and take notes. What questions do you ask in the first few minutes? What objections do prospects raise, and how do you respond? Which proof points – like customer success stories, ROI stats, or product features – do you highlight, and when? Pay attention to moments when prospects seem engaged versus when they lose interest.
To make sense of this data, create a simple spreadsheet. Include columns for qualifying questions, objections, proof points, demo flow, and outcomes (won or lost). After analyzing 20 calls, you’ll likely notice recurring themes. For example, you might find that you consistently ask the same 8–10 qualifying questions or that certain objections come up repeatedly. You might also see that deals close more often when you share specific customer results instead of focusing on features. These patterns will help you identify which techniques are teachable and which are unique to your personal style. Use these insights to shape your sales playbook.
Create a Sales Playbook That New Reps Can Follow
With your call analysis in hand, it’s time to build a sales playbook – a step-by-step guide to closing deals. This playbook will serve as an essential resource for your new hires.
Start by defining your ideal customer profile (ICP). Look at your past deals and outline key criteria like company size (by employees and revenue), industry, technology stack, buying triggers, and decision-maker roles. For example, instead of a broad description like “tech companies,” specify something like “mid-market B2B SaaS companies with 50–200 employees that use Salesforce.”
Next, document your qualification questions – the 8–10 questions that help determine if a prospect is worth pursuing. Organize these around budget, authority, need, and timeline. Examples include: “What’s your current process for solving [problem]?”, “Who else is involved in the decision-making process?”, and “What happens if this issue isn’t resolved soon?” Explain why each question matters so new reps understand what to look for.
Outline your deal stages with clear exit criteria for each phase. A typical B2B SaaS sales process might look like this: Initial Contact → Discovery Call → Demo → Proposal → Negotiation → Closed Won. For each stage, define what needs to happen before moving forward. For instance, a discovery call should identify the prospect’s pain points, budget, and decision-making process. Similarly, a demo should clearly showcase relevant ROI before wrapping up.
Lastly, include a section on common objections and responses. List the 5–6 objections you hear most often, like “It’s too expensive” or “We’re already using another solution,” and provide effective responses. This gives new reps a strong foundation while they develop their own style.
Choose Your CRM and Sales Tools
Your CRM is the backbone of your sales operations, keeping track of deals, conversations, and customer interactions. As you transition from founder-led sales to a team-based approach, choose a CRM that balances functionality with ease of use. Two popular options for early-stage SaaS companies are HubSpot and Salesforce.
HubSpot is a great choice for founders making their first sales hire. Its free tier covers basic contact management and deal tracking, while the Sales Hub Professional plan adds features like email sequencing, meeting scheduling, and intuitive reporting. It’s easy to set up and helps new reps adapt quickly, though it may have limitations as your company scales.
Salesforce, on the other hand, offers a more customizable and powerful solution. However, it requires more time for setup and configuration, making it better suited for companies with complex sales processes and longer cycles.
Here’s a quick comparison of the two:
| CRM | Best For | Cost | Setup Time | Scalability |
|---|---|---|---|---|
| HubSpot | Early-stage teams with simpler processes | Affordable (free tier) | Quick (1–2 weeks) | Great for initial growth |
| Salesforce | Complex, customizable sales needs | Higher per-user cost | Time-intensive | Ideal for larger enterprises |
Beyond your CRM, consider tools for email sequencing, proposal generation, calendar scheduling, and AI-powered lead scoring. AI tools can help prioritize high-value prospects, enrich contact data, and even suggest personalized email openers. Some CRMs now offer AI features that log calls, recommend follow-ups, and draft emails based on conversation context.
Make sure all your tools integrate with your CRM to keep your pipeline organized. Start with the basics, and expand your toolkit as your needs grow.
How to Hire Your First Sales Rep Without Making Expensive Mistakes
Hiring your first sales rep is a big decision – and it’s not cheap. With total compensation ranging from $160,000 to $200,000, a poor choice can set you back significantly, both financially and in terms of lost time. Many founders make the mistake of hiring someone either too senior, expecting them to build the entire sales function, or too junior, leaving them without the skills to close deals effectively.
The ideal first hire? A mid-level Account Executive who can juggle two key roles: spending about 60% of their time actively selling and the rest helping to shape your sales process. They might not have all the answers on day one, but they should have the experience and adaptability to close deals and quickly get up to speed with your product.
For more tips on building AI-driven sales systems, join our AI Acceleration Newsletter. In the meantime, here’s how to avoid expensive hiring mistakes and set up your sales process for long-term success.
What to Look for in Your First Sales Hire
Your first sales hire needs to bring a mix of skill, experience, and enthusiasm for your product. Ideally, you’re looking for someone with 3–5 years of experience carrying a quota and selling B2B products with an average contract value (ACV) between $50,000 and $200,000. This background ensures they’ve faced real objections, navigated complex buying processes, and closed deals without relying on the reputation of a big-name brand.
Candidates who’ve worked at mid-stage startups (Series A or B) are often a great fit. These environments require reps to build processes from scratch rather than simply following established playbooks. Look for someone who thrives in ambiguity and can handle challenges like technical hiccups during a demo or a lack of polished sales collateral.
Passion for your product is critical. In interviews, pay attention to whether candidates ask insightful questions about customer pain points and your solution, rather than focusing solely on things like territories or commission structures.
How to Interview and Evaluate Sales Candidates
Once you’ve outlined the ideal profile, it’s time to evaluate candidates thoroughly. Focus on three main areas: their experience, alignment with your product, and ability to execute sales strategies. Instead of relying entirely on recruiters, tap into your network and conduct targeted LinkedIn searches to find strong candidates.
In the first interview, dig into their past deals. Ask questions like, “What problem was the customer trying to solve? How did you position the solution? What objections did you face?” This will help you gauge how well they understand customer needs and whether they can navigate complex sales situations. Also, ask about their prospecting strategies: “How do you build a pipeline when marketing isn’t delivering enough leads?”
In a follow-up interview, run a mock discovery call. Give them a brief customer scenario and let them lead a 15-minute session. This exercise will showcase their ability to ask the right questions, listen actively, and identify customer needs. Finally, don’t skip reference checks. Ask former managers about their performance, adaptability, and whether they’d rehire them. Pay attention to lukewarm responses – those can be a warning sign.
Setting Base Salary, Commission, and Quota Ramps
To attract the right talent, structure compensation with a 50/50 split between base salary and variable pay. Offer a base salary of $80,000 to $100,000, with an equal amount in commission, for total on-target earnings of $160,000 to $200,000.
Design a quota ramp that accounts for the time it takes to onboard and get up to speed. For the first three months, don’t set a quota – this period should focus on learning. From Month 4 onward, gradually increase the quota: 25% in Month 4, 50% in Month 5, 75% in Month 6, and 100% by Month 7. For example, if the annual quota is $800,000 (about eight deals at an ACV of $100,000), this ramp gives the rep time to build momentum.
When it comes to commissions, keep it simple. Pay a fixed percentage on closed deals once the contract is signed and the first payment is received. Avoid complex tiered structures or accelerators in the first year, as you’re still figuring out what top performance looks like. Expect to invest around $200,000 in total, with noticeable returns starting around months 6–7. This approach ensures your first hire not only contributes but also becomes a key part of scaling your sales efforts from founder-led to a team-driven model.
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The First 90 Days: Onboarding and Managing Your First Rep
Your first sales hire is in place – now it’s time to get them up to speed without losing momentum. Many founders either push new hires into selling too soon or keep them in training mode for too long. The key is finding the right balance: structured learning combined with hands-on selling, all while tracking specific activity metrics to measure progress before expecting closed deals.
Month-by-Month Onboarding Plan and Activity Goals
Days 1–30: Learning the Ropes
The first month should focus entirely on learning, not selling. Your new hire needs to understand your product, grasp customer pain points, and learn how to handle objections. Have them shadow your sales calls and review essential product materials. Don’t set quota expectations just yet. Instead, track their ability to clearly articulate your value proposition and ensure they complete any required product or process certifications.
Days 31–60: Taking the First Steps
In the second month, your rep should start dipping their toes into selling. They can begin conducting discovery calls with you on the line, building their own pipeline, and experimenting with messaging strategies. Role-playing becomes a critical tool here – spend about 30 minutes each week practicing responses to common objections. During this phase, focus on activity metrics like completing 10–15 discovery calls, demos, or proposals per month.
Days 61–90: Making an Impact
By the third month, your rep should begin managing deals from start to finish. You’ll still be available for support, but they should take the lead. At this stage, they’ll follow up with prospects, refine their negotiation skills, and work with internal teams to handle objections. While a closed deal may not happen until month four or five, they should maintain a healthy pipeline by day 90, with clear next steps recorded in your CRM for all active opportunities.
These milestones provide a roadmap for onboarding success. Use weekly reviews to fine-tune their performance along the way.
Weekly Pipeline Reviews and Coaching Sessions
Set up a 30-minute pipeline review every week. These sessions should focus on reviewing active opportunities in your CRM. Discuss the customer’s pain points, identify decision-makers, and address any obstacles slowing progress. This isn’t about micromanaging – it’s about spotting trends and reinforcing effective strategies.
Dedicate part of each session to role-playing. For example, if a prospect says, “We’re not ready to buy right now,” work together to uncover their concerns and practice alternative responses. Studies show that practical exercises like this can improve performance by 22%.
Track both leading indicators (calls made, emails sent, meetings booked, and follow-ups completed) and lagging indicators (opportunities created, pipeline value, and closed deals). During the first 90 days, focus on these activity metrics rather than expecting immediate results. Allow your rep time to build momentum, and avoid making drastic changes unless you see clear warning signs.
This structured approach ensures your new hire builds a strong foundation for long-term success.
When to Add to Your Sales Team and Shift Your Role
Hold off on hiring additional sales reps until your first hire has proven they can consistently deliver results and your sales process is repeatable. Once they’ve demonstrated steady performance, you can confidently scale your team. At this point, shift your focus from closing deals yourself to coaching and overseeing strategic initiatives. Empowering your team while refining your go-to-market strategy will set you up for sustainable growth.
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Conclusion: From Founder-Led to Team-Led Sales
Growing from $2M to $10M ARR means rethinking how you approach sales. At this stage, it’s no longer feasible to close every deal yourself. Instead, your focus shifts to building a system – a repeatable process that enables your team to deliver consistent results.
Here’s the game plan: start by systematizing your sales process before expanding your team. When hiring your first sales rep, choose someone who complements your approach, not someone to fully replace you. In fact, during the first year, you might still handle up to 50% of the deals while laying the groundwork for scalable success. Document your tried-and-true sales techniques, create a playbook for your team, and prioritize structured onboarding and coaching. Track the metrics that matter most and refine your process as you go. Want more tips on using AI to streamline this journey? Join our AI Acceleration Newsletter.
Once the foundation is set, technology becomes your ally. AI tools can take over tasks like lead scoring, follow-ups, and pipeline management, giving new reps a head start. These systems also offer real-time coaching and automate tedious work, helping your team ramp up faster and focus on what they do best – closing deals.
FAQs
How can I effectively document my sales process before hiring a sales team?
Start by reviewing recordings of your last 20 sales calls and demos. Pay close attention to recurring customer questions, common objections, and the strategies that consistently lead to closing deals. Use these insights to build a sales playbook – a guide that outlines the most effective steps, messaging, and tactics for your sales process.
At the same time, keep track of key metrics like lead sources, demo-to-close rates, and the length of your sales cycles. Compare these numbers to industry benchmarks – sales cycles often range between 40–60 days, with demo-to-close rates typically falling between 25–35%. This comparison can help you pinpoint areas that need improvement and monitor your progress over time. Documenting this information not only creates consistency but also lays a solid foundation for your first sales hire to hit the ground running.
What should I focus on when hiring my first sales rep?
When bringing on your first sales rep, focus on finding someone who is open to learning, flexible, and deeply aligned with your product and mission. Seek candidates who demonstrate strong problem-solving abilities, a natural curiosity, and the skills to create processes from the ground up.
The best candidates will have a solid track record in B2B sales, experience selling products within a similar price range, and the grit to navigate the uncertainties of a growing startup. Steer clear of hiring based solely on past sales numbers – what truly matters is their capacity to learn, work well with others, and build authentic connections with your customers.
How do I know when it’s time to grow my sales team?
When your sales team starts feeling overwhelmed, customer demand is climbing, or sales cycles are dragging out, it might be time to bring in reinforcements. Expanding your team can also make sense if you’re gearing up to enter new markets or roll out additional products – extra hands can help manage the increased workload.
Look for red flags like missed opportunities, delayed responses, or trouble keeping up with leads. These signs suggest that growing your team could help you stay on track and keep fueling your business growth.
