The SaaS Playbook Quotes

“The sweet spot for your work should be where all three intersect. If you’re focusing solely on things you’re good at that bring you joy, you can get stuck galloping down paths that are detrimental to the needs of your company. If you’re doing things the company needs that bring you joy (but you’re not good at), then you’re dragging your company down. But if you’re stuck doing things the company needs that you’re good at (but don’t like), that leads to burnout. That’s exactly what I was doing. I hired an executive assistant who lightened that load for a bit. She helped streamline a few things and made appointments, but what I really needed was someone to whom I could delegate at another level. At the time, I felt like we couldn’t afford someone who wasn’t contributing to the bottom line of the company. In retrospect, this was one of the biggest mistakes I made while building the company. I should have hired someone who could come into the office and handle operations. Things like legal, payroll, HR, and facilities. Most of these were outsourced to external providers, and it was just a matter of interfacing with them. As I look back at my descent into burnout, one thing that could have saved me was having enough funding to hire someone to do the work that didn’t bring me joy. Or prioritizing spending money on hiring and delegating tasks that didn’t move the business forward but were contributing to my lack of satisfaction at work. I hope you’re not at a place where the next section is helpful to you. I hope that you’re smarter than I was and are putting measures into place to keep yourself from burning out like I did. As Jason said in his talk: “The right question is what should you be doing differently now […] in order to build a company that’s more healthy and prosperous, and also avoid this balloon payment of emotional toil at the end.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“In your personal life, money saves you hours. In your business, money saves you years.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“White Labeling White labeling is when another company pays you to license your product and present it with its own branding, and the moment you launch a successful product, people will start emailing you with “exciting opportunities” to white label. For the most part, these conversations are a big waste of time. Usually what you have is someone who wants to start a business but can’t build their own product. They want to pay you per account they add, but they have no audience or distribution. In the end, you’ll spend a bunch of time talking to them, writing up contracts, and taking feature requests—for nothing. If you’re approached about white labeling by a large player, it’s worth having the conversation. You know they’re not wasting your time because they don’t want to waste their own. To justify the effort of white labeling, I recommend charging an up-front fee. We’re talking tens of thousands of dollars—$30,000 to $50,000 at a minimum. If someone balks at paying that fee, they’re not willing to put enough skin in the game to warrant your efforts. I’m not a fan of white labeling in most situations. It’s a way to serve customers and make money without building a brand. We discussed above how a brand is a moat, and losing that is an unfortunate consequence of white labeling.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“There are superpowers to being bootstrapped. One is that you don’t need anyone’s permission to start or build your company. Another is that your business doesn’t die until you quit. Bootstrappers don’t run out of money; they run out of motivation.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“There are many ways to ask customers why they churn. At Drip, any customer that canceled their account received an automated email within ten minutes of canceling. It said, “Hello, I’m one of the founders of Drip, and I’d love to hear why you decided to cancel your account.” We got a wide range of responses. Some people would tell us they were shutting their business down—which isn’t something we could fix. Others would say they switched to a cheaper tool because they didn’t need our more powerful product. Others switched to a competitor because they needed a feature we didn’t have.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Taking a Founder Retreat The two biggest things that have helped me in my journey as a founder are masterminds and founder retreats. Without those, I sincerely don’t think I would be as successful as I have been. My wife Sherry has a PhD in psychology. She started going on annual retreats after we had kids, where she got away for 48 or 72 hours without podcasts, movies, or books—just herself, a notebook, and silent reflection. When she first started taking retreats, it didn’t sound like my thing. I’m always listening to a podcast or an audiobook. I’m constantly working on the next project. But after seeing her come back from these retreats energized and focused, I decided to give it a try. I booked myself a hotel on the coast and drove out for the weekend with no radio, no project, no kids, and no distractions. Over the course of that two-and-a-half-hour drive, things began to settle. I started feeling everything I hadn’t had time to feel for the past year. In the silence, I had sudden realizations because I was finally giving them quiet time to emerge. During that retreat, it became obvious that my whole life had been about entrepreneurship. Ever since I was a kid, I have wanted to start a business. I’ve always been enamored with being an entrepreneur and the excitement of startups. I realized that I was coming to this decision of what to do next because of the idea of wanting to get away from the thing that had caused me to feel bad—as though startups were at fault rather than the decisions I made. At that time, my podcast had more than 400 episodes, which had been recorded over eight years. That wasn’t an accident. It existed because I loved doing it. I showed up every week even though it didn’t generate any revenue. During my retreat, I realized that being involved in the startup space is my life’s work. The podcast, my books and essays, MicroConf—all were part of my legacy. Instead of selling it off and striking out in a new direction, I decided to double down. Within a couple months, I launched TinySeed. Then I leaned into the next stage for MicroConf, where we transitioned from a community built around in-person events to an online and in-person community, plus mastermind matching, virtual events, funding, and mentorship. I also began working on this book. As a founder, it’s important to know yourself. Even if you started out with firm self-knowledge, the fast pace and pressure of bootstrapping a business—not to mention the pressures of the rest of your life—can make it difficult to see your path. A founder retreat is a way to reacquaint yourself with yourself every so often. After my first founder retreat nearly a decade ago, I started going on a retreat every six months. Now I do one a year, and it’s one of the most important things I do for myself, my business, and my family. If you’re considering a retreat, several years ago Sherry wrote an ebook called The Zen Founder Guide to Founder Retreats that explains exactly what questions to ask yourself, the four steps to ensuring you have a successful retreat, the list of tools she recommends bringing along, and how to translate your insights into action for the next year.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Getting through Burnout I’ve heard burnout manifests itself differently in different people, but for me it felt like a mix of depression and frustration. Not the kind you can clear up with a weekend away, but a long-term, deep sense of tiredness, lack of motivation, and feeling just a little pissed off at all times. This led to my aforementioned stints of staring at Trello for hours and a lack of presence at home. I would be home with the family, but most of the time my mind was elsewhere. I tell this as a cautionary tale: if you find yourself listless, unmotivated, or constantly frustrated as you endure the stress of building your company, it’s unlikely to fix itself. The best remedy for burnout is significantly changing your habits and patterns related to work, including stepping away for weeks, which feels like the last thing you can do when everything is going crazy (whether it’s good crazy or bad crazy). If you find yourself in this situation, you need to address it, or it will get worse. If unaddressed, burnout can lead to terrible outcomes, including long-term damage to your brain. If burnout is a situation you find yourself in, consider reaching out to a professional who works with founders on the mental game of entrepreneurship. Dr. Sherry Walling is one (she happens to be my wife, and she knows her stuff), but there are many other executive coaches and therapists who work with high-performing individuals to manage stress, burnout, and everything else that comes with our line of work. I’ve only started to touch on burnout here, but for an entire chapter about it, check out my third book: The Entrepreneur’s Guide to Keeping Your Sh*t Together: How to Run Your Business Without Letting it Run You.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“There are three clear benefits of being a part of a mastermind: Growth. By surrounding yourself with folks who can provide you with informed advice, qualified referrals, and critical constructive feedback on your failures in a safe space, you are setting yourself up with the resources and guidance you need to focus on growing your business. Hopefully there’s at least one other person on each call who has more experience in a specific area than you do. There are some things in my business that I’m pretty damn confident I’m good at. But I know I have blind spots in other areas. I can bring those things to my mastermind because they don’t have the same blind spots. Accountability. As many solo founders know, keeping yourself accountable with no outside forces can be challenging. During most mastermind meetings, there is a point in time when each member is in the hot seat, discussing past goals and their progress, setting new goals and tracking them, and reporting back to the other members with updates along the way. By asking your group to keep you accountable to your business, you’re also committing to holding them accountable. A good mastermind also forces you to look at your weaknesses. You can bring your weakest attributes in front of this small group of trusted individuals who know your story, your revenue, your growth rate, and all your foibles—personally and professionally. Your mastermind will tell you things that if your spouse said them, you’d ignore them. (Ask my wife about that.) Support. Humans are social beings. Napoleon Hill says that the convergence of two individual minds creates a third, invisible force that combines the strength of both of its components. When you share your vulnerabilities and successes with others, you magnify your own experience and make it the experience of those around you. The power that comes from those shared experiences can be just as compelling and empowering as your individual success. Three of my favorite entrepreneurial communities are Indie Hackers, the Dynamite Circle, and of course, MicroConf.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“raising funding also has the potential to save you years. As Craig Hewett, the founder of Castos, told me, funding allows you to “live in the future” by making investments you otherwise would have had to wait for. When Craig Hewett raised money for Castos, he spent it on hiring senior sales and development team members rather than the juniors many startups are forced to hire because of a lack of cash. This allowed Castos to make progress fast. Ruben Gamez, the founder of SignWell, used funding to invest in compliance (SOC2 Type 2 and HIPAA). They would have done so eventually, but they wouldn’t have been able to afford it until later. This investment allowed them to start closing major deals sooner and grow faster. Strategic hiring can be another way to spend funds. Jordan Gal, the founder of Rally, hired a chief of staff almost from day one. He told me, “Money allows you to hire in such a way that you, as the founder, can focus on whatever your superpower is, with far fewer distractions than when bootstrapped.” Derrick Reimer of SavvyCal burst into a crowded scheduling space by investing funds into SEO and marketing earlier than he would have been able to if he was purely bootstrapped. This potentially shaved a year or more off his marketing efforts. Those are just a few of the ways funding can help when applied strategically.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Don’t Torch Your Cap Table Your capitalization table is a list of who owns what percentage of your company. Literally: Rodrigo owns 70%, Janine owns 20%, and Fred owns 10%. Your cap table can get complicated if you start taking multiple rounds of investment. I’ve seen cap tables with 40 entries, where the founder still owns 50% of the company, a bunch of angel investors own 5% each, and early employees each own 1% to 2%. A complicated cap table isn’t a deal breaker. But you can torch your cap table if you let early investors or founders take too much of the company. We’ve had multiple companies we’ve been unable to fund because of their cap table. One was a company where the founder only owned 30% because he’d given up 70% to an agency he was working with in the early days. Another founder gave 60% of her company to an early investor who had only invested $50,000. When you let early investors take too much, you end up shooting your business in the foot by making it uninvestable. You also put the majority of the profits into someone else’s pocket. You can also torch your cap table by not vesting founder equity. If you start a company with two other people and split it equally, but six months later one of your cofounders gets a full-time job and leaves, they still own 33% of your company. You and your remaining cofounder are stuck working the next five or 10 years growing a company and putting money in your ex-cofounder’s pocket. This also creates a problem if you want to raise money. Normally in first-round funding, investors want to make sure the founders who are actively working on the business own 80% to 90% of it. This can be fixed with vesting, where you get zero shares during the first year you work at the company and 25% of shares after the first year, then the rest drip out over the next three years. Those numbers can vary—you might decide to say it’s three years to vest. Just make sure to talk to a lawyer when you set it up.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“There are many ways to ask customers why they churn. At Drip, any customer that canceled their account received an automated email within ten minutes of canceling. It said, “Hello, I’m one of the founders of Drip, and I’d love to hear why you decided to cancel your account.” We got a wide range of responses. Some people would tell us they were shutting their business down—which isn’t something we could fix. Others would say they switched to a cheaper tool because they didn’t need our more powerful product. Others switched to a competitor because they needed a feature we didn’t have. The key to getting useful data points out of an exit survey is to keep it short and direct, create a connection (“I’m the founder, and your feedback would help me build a better product!”), and ask for a reply—even if it’s just four or five words. This can give you a glimpse into what potential customers want, which helps guide product decisions. More often than not, you can get a quick win with churn using tactics like an email welcome sequence and in-app onboarding tools to make sure new users see value early. However, pushing churn below 2% or 3% is a long road that unfolds slowly as you refine your marketing and sales language, learn more about your ideal customer, and add more features those customers love (we covered that in the Market chapter).”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“It’s Taking Customers Too Long to Find Value. If customers aren’t seeing value in your product, it could be a matter of education. The standard approaches are to send onboarding emails to orient them to your product (see Val Geisler’s Dinner Party Strategy) and to hire a customer success manager to walk new accounts through the onboarding process (assuming their price point makes this worthwhile). When you have a high price point, hiring someone to help with onboarding can go a long way toward helping your customer find value. Essentially, you’re trying to help new customers find your minimum path to awesome (MPA). Basically, the moment when everything clicks and your customer says, “This is amazing!” For a social media scheduling app, maybe it’s when they load the first few posts and realize they can sit back and let your product take care of the rest. For an email product, it could be the minute they get a form installed on their website and start seeing new subscribers. It’s not always easy to find the MPA. Your product might be so complicated that there are many paths to seeing value. In that case, the burden is on you to educate your customers about how to get the most value in the shortest amount of time. One way to shortcut the process is to interview customers who are actively using the product and ask them when they first realized how your product would help them. With Drip, we even built a custom internal dashboard to track where trial users were along the path to awesome. Had they created their first email list? Installed a form on their site? Activated that form? I could watch individuals or groups of users go through those steps during the trial phase and see a leading indicator of how many were likely to convert into paying customers.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Generally speaking, the lower your product’s price point, the higher your churn. Some of the TinySeed companies that cater to hobbyists or very small businesses have churn in the 5% range, and while I’d love to see churn lower than that, it’s okay because they are in massive markets and have a very low cost to acquire new customers. For most companies like the type we’re discussing in this book, I suggest shooting for gross revenue churn as low as possible, certainly under 3% per month. At the venture scale, successful companies have less than 1% gross churn.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Asking for Referrals. Not every product can have word of mouth baked into the product, but every founder can—and should—be proactive about asking for referrals. When you see that trials are converting well and customers are happy with your product, set up an automated email that goes out around the 60- or 90-day mark. Say something like, “So much of our business is based on referrals. If you’re enjoying our product, could you please pass the word along?” The automated email works well when you have a pretty hands-off, low-touch sales process. However, for products with higher ACVs and a more intensive sales process, it’s better to ask for referrals in person.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“LOW: Churn Churn is the percentage of people canceling their subscription each month, and it’s the Achilles heel that kills (or plateaus) SaaS apps. If you can keep churn low, growth is much easier. If churn is high, it’s a force that’s very hard to outrun. Focus on revenue churn. To calculate this, divide the gross MRR that canceled in a given month by the starting MRR for that month: As a general rule, for most bootstrapped B2B SaaS businesses: Gross churn > 10% = Catastrophic Gross churn 8–10% = Not Good Gross churn 6–7% = Meh Gross churn 4–5% = Fine Gross churn 2–3% = Good Gross churn < 2% = Great With this caveat: if you are focused on high-priced contracts, say, above $25,000, your churn should be lower than the chart above. In that case, I’d categorize fine churn as 2–3%, good churn as 1–2%, and great churn at or below 1%. Churn is such a critical metric because it helps you calculate when revenue will plateau. At some point, the number of new customers you acquire will equal the number of customers you churn out each month. This causes your growth rate to effectively hit zero. You’ve hit your maximum number of customers (and revenue) that you can achieve without changing something in the business.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“LOW: Sales Effort Sales effort is a measure of the length of your sales cycle and includes the number of touch points required to make the sale. Where CAC measures the amount of money you’re spending to get a new customer, sales effort measures the time and energy you’re spending. The best way to track sales effort is to look at both the average number of days from someone scheduling their first demo to closing and the number of calls it takes to close a deal. Your ability to keep sales effort low depends greatly on your industry and customer base. If you’re doing enterprise sales, your sales cycle will be long and require more effort than if you’re targeting solopreneurs and other small businesses with a single decision-maker. A three- or four-month sales cycle is reasonable in enterprise sales—and worth it because the ACV might be $50,000. If you’re spending that much time for $5,000 contracts, though, that’s rough. No matter what your sales process looks like, you want your sales effort to be as low as possible. Here are some ways to lower this number. Self-Serve Sign-up and Onboarding. Many inexpensive products can get away with low price points because they have a low-touch or no-touch sales process. They have a self-serve sign-up and onboarding process, which requires almost no sales effort. The higher your ARPA, the less likely they are to become customers without some sales effort. But finding places to offer self-service along the journey can reduce the amount of hand-holding your team has to do while making the process speedier for your customer. One-Call Close. Self-service isn’t going to work in a lot of spaces, but you can try to get to a point where the decision is made by a single person. You can do this by targeting a founder, a developer, or a single manager. You can also streamline the back-and-forth of providing more sales materials, getting on second calls, waiting for input from the committee—and on and on. Educate your customers as much as you can ahead of time so they have the information they need and develop checklists to gather the information you need to close the deal quickly.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“LOW: Cost to Acquire a Customer (CAC) In its simplest form, CAC is all the costs associated with landing new customers (e.g., marketing, advertising, sales) divided by the number of customers you acquired during that period. It’s sometimes tricky to calculate because getting a handle on your marketing costs can be tricky. If you’re focusing on SEO, you may be creating all the content yourself rather than paying a writer. You may be getting a lot of your early customers from forums you spend time on or by getting in front of other people’s audiences. In those cases, the cost is your time rather than an easy-to-calculate number. It’s a lot simpler to calculate CAC if you’re running ads. Then, you can see how much you’re paying per click and track how many people convert from each source. But if you’re not in that position, valuing your time at a certain rate (e.g., $150 an hour) and taking your best guess at time and money spent on marketing in a given month can get you to a good enough estimate of your CAC. How do you know if your CAC is too high? By calculating how long it’ll take to pay back the costs of acquiring each customer. As I was first getting into recurring revenue, I thought that if I was getting $1,000 in LTV from each customer, I could spend $700 to acquire every customer and make $300 a pop. Right? The problem is that you’re not getting $1,000 every time you sign a new customer. With a $50-a-month contract, you’re getting that $1,000 over the course of the next year and a half. If you spend $700 per new customer in January, you won’t break even on those customer acquisition costs until next February (assuming the customer doesn’t churn). With venture capital, the rule of thumb is that you should spend no more than one-third of your customer’s LTV or no more than one ACV. As bootstrappers, we don’t have enough cash to wait 12 months to recoup CAC from every customer. Most successful bootstrappers I know are in the two- to six-month payback period (depending on how much cash they have in the bank). There are times when that number can get more aggressive. For example, at our peak with Drip, we could afford to spend more on customer acquisition because we had the cash in the bank and I knew the numbers in the rest of our funnel by heart. Even at our peak, though, we were only running seven or eight months out—that’s the high end for bootstrapped companies.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Task-level thinkers are team members who focus on their current or next task. They might be early in their career or get overwhelmed with more than a few sequential tasks on their plate. Most of us begin our careers as task-level thinkers because prioritizing many complex, interrelated tasks is often not a natural ability. Project-level thinkers look ahead weeks or months and juggle multiple priorities. They often rely on team members to complete work that’s combined into a single deliverable. Project-level thinkers have advanced systems in place to track the myriad moving parts needed to successfully complete a project. Owner-level thinkers not only manage projects but also think about how to improve internal processes and bring ideas for experiments that can change the trajectory of the company. Owner-level thinkers look ahead months or years and consider strategic shifts that may need to take place to take the company to the next level.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Craig Hewitt, the nontechnical founder of Castos, told me, “If I did it again, I’d very much want my first developer to be a cofounder or someone I know really, really well. I’ve wasted too much money while being misled by developers who are just looking to make a few bucks and don’t care about the outcome of the project.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Don’t Invent Job Titles I used to make up job titles because, as a bootstrapper, I didn’t particularly care what someone’s title was. I didn’t want it to matter—but it really does. When we realized we needed an architect to scale our infrastructure at Drip, we asked our internal recruiter to hire for the job of “Senior Scaling Architect.” She eventually talked us into the title of “Senior Architect.” Why? Because when she ran the data, she couldn’t find enough salary information on the title we’d given her. Not only that, but if we’d used a made-up job title, qualified candidates wouldn’t have known what we were hiring for. There are standard SaaS job titles. Use them. Your ideal candidates have saved job searches for things like “Engineer,” “Customer Service Lead,” and, yes, “Senior Architect.” Ignoring that makes it harder to connect with people searching for the job you’re hiring for. It also does a disservice to whomever you end up hiring. They’ll have a much tougher time explaining their qualifications to their next employer when their job title was “Code Wizard” rather than “Senior Engineer.” Although a treatise on organizational structure is beyond the scope of this book, here’s a typical hierarchy of engineering titles (in descending order of authority) that can be easily translated into other departments: Chief Technical Officer VP of Engineering Director of Engineering Manager of Engineering Senior Software Engineer Software Engineer Junior Software Engineer Entry-Level Software Engineer Note: These titles assume the typical path is to move into management, which doesn’t have to be the case. Individual contributor titles above Senior exist, such as Principal Engineer and Distinguished Engineer. But for the sake of simplicity, I’m laying out the above hierarchy, which will work for companies well into the millions of ARR. Another note on titles: be careful with handing out elevated job titles to early employees. One company I know named their first customer service person “Head of Customer Success.” When they inevitably grew and added more customer service people, they didn’t want him managing them and ended up in a tough situation. Should they demote him and have him leave? Or come up with an even more elevated title for the real manager?”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“You need a good process for qualifying prospects before they get to you so you’re not stuck doing demos with people who will pay you $30 a month or are the wrong fit for your product. Dialing in your positioning, website, and marketing is one way to make sure you’re attracting the right prospects and weeding out those who aren’t a good match. Using a qualifying form to schedule a demo is also good. Have them put in the company’s name, the company’s size, their best work email, and other information you need to know. Weeding through those prospects can be time-consuming—especially if you have a dual funnel with low-priced and enterprise-level tiers. Here’s a hack: At Drip, anytime someone clicked “Book a Demo,” they got a pop-up that asked for their name and value metric (i.e., how many subscribers they had). If they put in a low number, they were redirected to a page with a video demo, a 10-minute screencast of me walking through the product. If they put in a high number, they were directed to our scheduling link to book a time for a more extensive conversation. As Drip grew, the cutoff number for in-person demos grew, too. At first, we were doing demos for people in our lowest tiers because it was early and we wanted to learn about our market by talking to anyone we could. Bit by bit, we ratcheted up the number on the form based on how many salespeople had the bandwidth to run demos.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“When Should I Hire Someone to Take over Sales? Hiring someone to help you with sales comes down to whether you’re good at it and whether you enjoy it. If you’re good at sales, it makes sense to keep doing it until sales conversations are encroaching on the rest of your founder responsibilities. If you’re bootstrapping, you have to hustle in the early days until you have the money to hire someone. But by the time you have five or six employees, you probably should only be involved in large deals. Sales demos are usually easy to teach, and as a founder, your energy will be better spent elsewhere. One thing to note is that if most of your leads are warm, inbound leads, you can actually combine the sales role with customer success. This works best when your prospects already have some sense of your product and are just trying to understand whether or not it’s a good fit for them. Your customer success/salesperson will be there to show them around and answer questions rather than lead high-pressure sales calls. If it’s more cold/complex sales, you’ll want a salesperson incentivized by commission.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Demonstrate How Your Tool Solves the Problem Thinking of yourself as a problem solver first helps solve another common issue I see with sales demos. Instead of giving prospects a painfully detailed explanation of every feature, only show them the relevant parts. Software demos are not tours of your product. You don’t need to take a deep dive into all your settings and obscure integrations, no matter how proud you are of them. Instead, think of a sales demo less as a presentation and more as a conversation. You should be asking questions and listening more than talking. For more on sales demos, I recommend the book Product Demos That Sell: How to Deliver Winning SaaS Demos by Steli Efti.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Follow Up It’s amazing how many salespeople don’t bother following up. People are busy, and following up until someone tells you they are no longer interested is the process that good salespeople follow.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“With B2B SaaS, sales shouldn’t be sleazy. Instead, it should be an educational conversation. My TinySeed cofounder Einar Vollset says, “When selling SaaS, think of yourself as an unpaid expert who’s helping the prospect solve their problem using software.” You’re not trying to force a fit between your software and your prospect’s problem. You’re putting on your consultant hat to help your prospect define their problem and come up with a good solution. Thinking of yourself as an expert problem solver first sets a good tone for sales demos. When I used to do sales demos, I would introduce myself as the founder and say, “I’m not trying to talk you into anything. I’d just love to show you our tool and get your feedback on how it might fit your needs.” If your tool doesn’t fit their needs, it’s far better to let that prospect move on (maybe with a recommendation for a tool that’s a better fit) than to pressure them into signing up. Don’t waste time or money onboarding someone who’s just going to churn out after a month or two. Qualify before You Demo There are few things worse than showing up to a sales call to find out the person doesn’t have the budget or the need for your product. As someone with intimate knowledge of customers who buy your software, you should have a good idea of the common threads that link them. Asking even a few questions about budget, timeline, and the problem they are trying to solve can be a window into whether it’s worth your time to jump on a demo. Have a Script Even though as the founder you can run a demo with your eyes closed, if you have a standard script, you are always ready to train someone new to take over sales. Say No to People Who Aren’t a Fit If you know someone will not get value from your product or believe they will be a problem to support, do not be afraid to let them know you don’t think they are a fit and recommend competing tools. If you are qualifying people in advance of your demo, this shouldn’t be something you have to do often, but forcing a sale only to have a customer churn out a few months later will waste a lot of resources.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“You can also talk to their past employees to get the inside scoop. I’ve reached out to former employees of competitors on LinkedIn to say, “I’ve built a competitor to your former employer, and I’d love to chat about what’s working in our industry when it comes to marketing.” I make it clear they don’t have to tell me any secrets they don’t feel comfortable sharing, and I’ve even offered to pay them for their time. Salespeople especially love to network—and talk. They’re often a fount of knowledge about what sales brochures look like, how the marketing team works, and what your audience is looking for.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Once you’ve narrowed down your list of potential approaches, you can use any prioritization framework to sort them. I’ve found the ICE framework helpful for this purpose. ICE stands for: Impact: If this works, how big will the potential impact be? Confidence: How likely is this to succeed? Ease of implementation: How easy is this to execute? ICE is often used to prioritize feature development, but it’s also a good tool for prioritizing marketing. To do this, list potential approaches in a spreadsheet and rate them on a scale of one through 10 for each of the above characteristics. I’ve seen people use several methods to get the score. Score = Impact x Confidence x Ease: This gives you a score with an exponential impact. In other words, the higher you rate any one area, the more confident you need to be. Score = (Impact + Confidence + Ease)/3: This gives you an average of these three scores. However you rank those facets, using the ICE framework is a way to get your approaches into a spreadsheet and figure out which are the best to start with. You can list things by high-level approaches (content marketing, PPC) or by individual tactics (ebook, blog post, guest posting, YouTube ads, Facebook ads). You can also start by ranking high-level approaches, then start a new tab in the spreadsheet to break down the top approaches by individual tactics. Then tackle the highest-rated approaches and tactics first.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Other People’s Audiences. This involves putting yourself in front of established audiences through guest posts, podcast tours, and YouTube tours.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Content Marketing. Although it is often coupled with SEO, content marketing relies solely on virality or on building an audience slowly over time, without the long-term benefit of organic search. This includes writing blog posts you hope will make it to the top of social news sites like Hacker News and Reddit and building a media brand alongside your product (something I recommend only for very well-funded companies). It also includes producing content to educate people at different steps in their funnel whom you already have permission to contact. Most people think of blog posts when you mention content marketing. However, content can include books, ebooks, audio (think podcasts), video (think YouTube), or even in-person courses that are given away to bring links, traffic, and leads and build credibility. Most founders start by producing the content themselves, then hire people to help with production later.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital

“Q&A Sites. This approach focuses on answering questions on Quora, Stack Exchange, and other relevant Q&A sites.”
― Rob Walling, The SaaS Playbook: Build a Multimillion-Dollar Startup Without Venture Capital