SaaS

How This Multi 7-Figure Entrepreneur Sold 400+ Sub-Accounts: How to Sell Your Business Software as SaaS

Charles Higgins

Charles Higgins

— 12 min read
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In our original interview with entrepreneur Kayd Welke, we walked through the exact blueprint we used to grow a multi–7‑figure business and sell more than 400 sub-accounts of our business software. We ran companies across a wide variety of industries, learned how to systemize everything, and turned recurring revenue into a predictable foundation for growth. This article breaks down what we did, why it worked, and precisely how you can replicate the most practical parts without overcomplication.

Table of Contents

What you’ll learn in this guide

  • How we moved from a single local business to hundreds of recurring customers.
  • The exact systems, delegation rules, and automations that kept us from burning out.
  • Simple outreach tactics that win customers without big ad budgets.
  • How to reduce churn with onboarding and support that actually works.
  • Key lessons from crises like payment processor shutdowns and partner failures.
  • Practical next steps you can implement in the next 30 days.

Who we are (short version)

We run multiple companies across services, retail, e‑commerce, and software. Our portfolio includes field service businesses (like pest control and garage-door services), moving companies, equipment rentals, photography-focused services, and a marketing agency. We also develop software tools and browser extensions to solve the everyday problems we encounter while running those businesses.

We’re operators first. We build, test, and sell solutions because we used them ourselves. That gives us credibility in the verticals we enter and makes selling easier—because we can speak the language of the business owner we’re trying to help.

How we packaged software as SaaS (and why it sold)

When you sell software to small businesses, there are two winning approaches:

  • Package the software with a service so businesses get immediate results and ongoing support.
  • Sell the software as a stand-alone solution that solves a specific pain point—make it so simple customers can see value instantly.

We started by combining both. We owned a pest control business and built automated workflows to handle lead follow-up, review capture, and appointment booking. Instead of just using the software internally, we packaged our automation and support together and offered it to other pest control companies. That combo—software plus done-for-you services—made the offer irresistible.

Why that worked:

  • We had domain experience. We weren’t a stranger selling a platform—we’d lived the problems our customers were trying to solve.
  • We delivered measurable outcomes (faster booking, more reviews, higher conversion). Those results reduced churn and increased referrals.
  • We kept the tech simple. Most customers only needed one or two features to see value, so we focused on a small, high-impact set of automations rather than trying to sell the whole product suite.

Start small: focus on one high-impact feature

We found that the fastest way to close a sale was to focus on the one thing that mattered most to the buyer. For many local businesses that was:

  • Lead follow-up and nurture automation
  • Automated review generation
  • Simple booking flows

We didn’t begin by pitching a massive all-in-one CRM. Instead, we offered a single, simple solution—often in person or within targeted social groups—and proved quick results. That one-feature approach is less threatening to busy owners and removes decision friction.

How we got our first customers

Because we owned and operated in the industry, our first customers came organically:

  • We used targeted online ads to replace door-to-door sales, generating leads consistently.
  • As we showed measurable results, peers and other business owners asked how we were doing it.
  • That led to training sessions—group and one-on-one—where we taught owners how to run the ads and configure automations. Many preferred paying us to do the work instead.

We ran paid group training (an eight-session program) and private consulting. The group program got businesses live quickly; the private option provided a faster, tailored onboarding. The combination helped us scale: training built authority and trust, while done-for-you services brought recurring revenue.

The operations playbook: systems, people, and SOPs

Scaling across dozens of businesses requires more than hustle. The three elements that made scaling possible for us were:

  • Systems: Repeatable workflows and clear automations for everything that didn’t need human judgment.
  • People: Hiring and trusting experts to own front-line work while we focused on strategy and growth.
  • SOPs: Step-by-step guides so any trained person could complete tasks without reinventing them every time.

The hardest skill to learn was letting go. We trained ourselves to accept that someone who does a task 80% as well as we would is 100% better than doing it ourselves forever. The goal is repeatable, predictable outcomes—not perfection on every task.

How we handled mistakes

We treated early mistakes as data. Our approach:

  • First, check the SOP or the instructions. Often the problem was unclear guidance.
  • If the instructions were correct, we evaluated whether the person needed more training or better placement in the organization.
  • We typically allowed three to four opportunities for improvement, but if someone consistently missed the mark we reassigned or replaced them.

That approach kept the team focused and fair. It’s treated as a team-building process rather than individual blame.

Outreach that actually works (without big ad budgets)

Our most underrated growth channel was participation in niche social groups. The sequence looks like this:

  1. Find discussion groups where your target customers ask operational questions (e.g., “how do I get more reviews?”).
  2. Answer questions by sharing practical value. Don’t sell on the first touch—build trust.
  3. Create short content (a video or help guide) that answers a frequently asked question and use it as a resource to send back into those groups.
  4. When someone asks for help, offer a free test, a short trial, or a low-commitment audit to get your foot in the door.

We also developed a browser extension to find relevant questions across the groups we were part of, gather them into a single list, and comment quickly from one place. That saved hours of manual searching and let us be the first helpful voice on many threads.

Offer and value—what matters most

Price is rarely the biggest lever for growth. The real lever is the perception of value. If your offer solves a problem and shows ROI, the price becomes a secondary consideration.

How to craft a winning offer:

  • Start with a high-impact result (more bookings, more reviews, automated follow-up).
  • Quantify the benefit: show a before/after where possible.
  • Bundle services and software if needed to lower the buyer’s risk and increase first-month impact.
  • Make onboarding fast—your first win should happen within days, not months.

Onboarding and onboarding experience—your best defense against churn

We discovered that churn isn’t just about the product—it’s about the early experience. Businesses who get a smooth start and a clear roadmap stick around longer.

Key onboarding elements that reduce churn:

  • Welcome message with a short video explaining next steps and setting expectations.
  • Clear action list for what the customer needs to provide (e.g., logos, access, phone number) and what we will do for them.
  • A 30-day roadmap with milestones and the customer’s first success metric.
  • Fast, knowledgeable support when something goes wrong.

When customers complete setup quickly and see early wins, retention improves substantially.

Support: keep it in-house when you can

We moved away from outsourced support and brought everything in-house. Why?

  • Industry-specific solutions require industry-specific support knowledge. Outsourced teams often support many clients and don’t learn the nuances of your product.
  • Faster resolution and contextual answers lead to happier customers and fewer escalations.
  • Keeping support close to product development helps convert recurring issues into product improvements and better documentation.

That said, if you’re starting lean, you can begin with an outsourced option—but plan to train them deeply or transition support in-house as you scale.

Handling big crises: partner problems and payment interruptions

We’ve been through everything—partners who couldn’t handle stress, people who disappeared, fraud, and payment processor shutdowns. The practical lessons we learned are simple and operational:

  • Always assume there’s risk in partnerships. Legal agreements, transparent reporting, and clear responsibilities reduce ambiguity later.
  • Keep backups for mission-critical platforms. If your primary payment processor is disabled overnight, have a secondary processor you can flip to.
  • Export and backup your customer and payment data regularly (every 30–90 days) so you can move between processors with minimal disruption.
  • Build a crisis checklist that includes communication to customers, short-term payment routing, and a recovery plan.

These steps are time-consuming but save you from the single event that can otherwise wipe out months of revenue.

Automation stack—what we automate first

We prioritize automations that remove repetitive work and directly increase revenue or protect margins. Typical high-impact automations include:

  • Lead capture and multi-channel follow-up (SMS, email, and phone reminders).
  • Automated review requests after a completed service.
  • Onboarding sequences with conditional logic so new customers see only what applies to them.
  • Support ticket routing and canned responses for common issues.
  • Financial backups and syncs to secondary payment gateways on a schedule.

Automation isn’t about replacing humans—it's about removing low-value tasks so your team can focus on higher-value work like sales, customer relationships, and product improvements.

Using AI thoughtfully

AI is useful for accelerating content creation, improving first-line support, and identifying frequently asked questions to build FAQs and training materials. The key is to train AI models on your company’s unique processes so responses match your voice and context. A properly trained AI assistant can cut support time and reduce repetitive questions—but we still keep a human in the loop for complex scenarios.

How to approach customers who already use another solution

Most small businesses are happy where they are unless something breaks or a better, easier solution appears. Our approach is gentle and non-confrontational:

  • Be helpful: If they’re using a competitor and it’s working well, acknowledge that and offer a helpful resource or audit.
  • Position for convenience: Explain one feature or outcome you can improve—don’t try to sell every capability at once.
  • Leave the door open: give your contact details and a low-commitment way to reconnect later.

People change vendors for reasons other than price: better support, a specific feature, or a smoother onboarding experience. Make sure you highlight those tangibles.

Scaling multiple companies without burning out

We follow a few practical rules to manage many businesses at once:

  • Every business runs on four pillars: product, marketing, sales, and support. When each pillar exists and is measured, you have a repeatable engine.
  • Create a simple launch checklist that includes the must-have automations and the minimum onboarding experience.
  • Hire a trusted general manager for each business who can run day-to-day operations while you focus on new opportunities.
  • Plan your day the night before to avoid decision fatigue and maintain momentum.

We also use a principle we call “ambitiously lazy.” That means we work hard, but always ask: “Is there an easier, more efficient way to do this?” If the answer is yes, we implement it.

Decision-making and avoiding analysis paralysis

Faster decisions lead to faster learning. We make decisions quickly, test them, and course-correct when needed. Common practices that keep us moving:

  • Time-block “decision time” in the calendar so choices aren’t made on the fly.
  • Limit options—too many choices cause paralysis. Choose between two or three well-researched options rather than a dozen.
  • Delegate routine decisions to trusted staff and reserve your bandwidth for high-impact strategy.

What we would do first if we started over

If we had to rebuild from scratch, we’d:

  1. Pick one industry where we already had domain knowledge.
  2. Join every relevant industry group and listen. Find the most common, painful question people ask.
  3. Create a single answer resource (video or guide) that solves that problem and promotes it in the groups.
  4. Offer a simple trial or free test to get early adopters and testimonials.

That approach is inexpensive and relies on attention and persistence rather than big ad budgets.

Short, practical checklist to replicate our approach

  • Pick a focused niche and list the top 5 questions owners ask in group discussions.
  • Create one high-impact automation (e.g., review collection or lead follow-up) and make the setup frictionless.
  • Offer a low-cost trial or short paid pilot so customers can see value in 7–14 days.
  • Document the onboarding process as an SOP and use it for each new customer.
  • Measure churn monthly and act on early warning signs (low logins, missing setup steps).

MRR Minute: Quick takeaways

  • Smartest investment: investing in ourselves through ongoing education.
  • Client success story that sticks: helping a brand-new business get off the ground using the same playbook we once needed.
  • Biggest lever for fast growth: the value in your offer—solve a real problem and show it.
  • One thing we stopped doing: getting trapped in day-to-day tasks; we delegated quickly.
  • One metric to track: churn—if churn goes down, everything else improves.

Real examples from our playbook

Here are three short case studies that illustrate the approach in action:

Case study: Pest control

Problem: Door-to-door sales were expensive and inconsistent.

Solution: We built targeted online campaigns paired with automation to nurture leads and request reviews. We offered training first and then sold a done-for-you package to those that wanted results without the learning curve.

Outcome: Rapid customer acquisition with strong retention due to recurring value from the software and support.

Case study: Trailer and equipment rentals

Problem: Small rental operators were struggling to find leads and manage bookings efficiently.

Solution: Focused outreach in niche groups, a simple booking automation, and an onboarding video that demonstrated the value in days.

Outcome: Over 40 customers in a few months using organic group outreach—no ad spend.

Case study: Photography platform

Problem: Photographers use fragmented tools for bookings, group management, and client communication.

Solution: We built an integration and a workflow tuned for photographers, plus a content strategy addressing the most common platform questions raised in industry groups.

Outcome: Rapid adoption from small studios that value domain-specific features and human support.

Pricing and transparency

Keep pricing straightforward: explain exactly what’s included, what’s optional, and whether there are any one-time setup fees. Customers prefer predictable billing and clear support expectations. We build our offers so there are no hidden fees—just the product, the support, and the outcome customers can expect.

Common objections and how we handle them

  • "We already have a provider": Acknowledge it, show one specific improvement you can deliver, and offer a low-risk trial.
  • "It’s too expensive": Focus on ROI and show how automations reclaim time and increase bookings or reviews.
  • "We don’t have time to set it up": Offer white-glove onboarding or a free setup week to remove friction.

FAQs

Q: How many sub-accounts should I aim for first?

A: Start with a goal of 10 to 100 depending on your capacity—100 is a realistic, meaningful milestone that validates product-market fit and covers basic recurring costs.

Q: Do I need to be an expert in the industry to sell software to that industry?

A: No—but domain knowledge helps. If you lack it, partner with a subject-matter expert or hire someone who has operated in the industry to speed up learning and reduce friction with prospects.

Q: Should I outsource support to save costs?

A: Not initially. Industry-specific support is a differentiator. Bring support in-house as soon as revenues allow so your team learns common issues and converts them into product improvements.

Q: What automation tools should I use?

A: Use reliable workflow and automation platforms that let you connect systems and build repeatable flows. Prioritize tools that are easy to maintain and export data from—don’t lock yourself into a provider that makes data extraction difficult.

Q: What do I do if my payment processor shuts down my account?

A: Keep a secondary processor and export customer payment data regularly (every 30–90 days). Have a contingency plan that includes communications templates and quick steps to switch payment routes so customer service impact is minimal.

Q: How do I reduce churn fast?

A: Improve onboarding so customers see value quickly, provide proactive support, and create regular check-ins during the first 30–90 days. If a customer wants to cancel, always ask why and offer short-term fixes or education resources; many cancellations are solvable.

Final thoughts: keep it simple and do the work

There’s no secret growth hack that replaces consistent execution. Start with a niche you understand, solve one pressing problem exceptionally well, make onboarding a frictionless experience, and keep support tight and helpful. From there, scale with repeatable systems, automate where it saves time, and delegate with clear SOPs.

We built 400+ sub-accounts and multiple seven-figure businesses by following that simple loop: find the problem, solve it simply, prove results, and scale the process. If you’re ready to start, pick one industry, pick one feature, and commit to getting ten customers in 90 days. The rest follows.

Take action today: choose one problem to solve for one niche, document a simple onboarding playbook, and start participating in the conversations your future customers are already having.

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