The SaaS sales process I used at Drip, which I sold in a life-changing exit
I'm self-aware enough to know that I’m not a great salesperson. But even if you don’t think of yourself as a salesperson, every founder needs to be able to sell — whether you’re talking to potential customers, trying to raise investment, or “selling” the company’s vision to new hires.
One of the most important parts of sales is nailing your sales demos. Below, I'll explain the process we developed at my last startup Drip — a process that evolved over several years and helped us grow Drip from nothing to millions in ARR and on to a potential life-changing exit.
Educate; don't sell
Sales shouldn’t be sleazy. Instead, it should be an educational conversation. I now run a startup accelerator called TinySeed, and my 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.
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.
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.
If possible, take payment over the phone
Giving a demo and hoping the person signs up through the web site is not a great way to close a deal. Not every SaaS application is a one-call close, but if yours is, set up their account at the end of your call, including taking their payment info over the phone.
Ask the right questions
Here are good questions to ask during sales demos:
1. What problem are they looking to solve?
Your demo is not a product tour; it’s proof you can solve their problem. Focus on the customer’s pain and how you can fix that.
Sometimes your prospect may be unable to clearly articulate the problem they’re trying to solve. Or they may come in thinking they’re trying to solve one problem when they actually need help with something else. The more conversations you have with prospects, the better you’ll be at consulting with them.
2. How are they solving that problem today?
Finding out what other tools and software they’re currently using to solve their problem helps you frame your solution relative to what they’re already familiar with.
For example, if they’re using Mailchimp, I could compare Drip’s features to what they already know. If they say Infusionsoft, I know they’re used to a more expensive and clunkier tool. If they say they have an Access database and they’re sending emails through a hacked-together system, then I could start by talking about the benefit of using an email service provider at all.
3. How big is their organization?
Are they a solopreneur with 500 people on their email list? A company with a few dozen employees? A Fortune 1000 company with an intense enterprise sales process?
Knowing this can help you understand how valuable this sale is to your company and how much value you’ll be able to provide to them.
4. How sophisticated is their understanding of this category?
Try to ask tactfully how much expertise they have so you can speak to their level. Again, when you’re thinking like an expert problem solver, your goal will be to educate your prospect. They should walk out of the sales demo better able to do their job — regardless of whether your product was a good fit.
One way to ask about their expertise is by going deeper into how they’re using other tools. For example, if a prospect tells me they’re using Mailchimp, I could gauge their sophistication by asking if they’ve used any of the automation features.
5. What’s the decision-making process?
Toward the end of a sales demo, it’s good to get a sense of who else needs to weigh in on this decision. Are you talking to the decision maker? Does your prospect need to go back to a group? Is there any collateral you can provide, like a PDF or a guide, that will help them champion your product to their organization?
Talk through the timeline of when you can expect to hear from them, when you should follow up, etc. Then, when the demo’s over, make sure they’re in some type of CRM so that you follow up at the right time.
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.
A hack to lower sales effort
Sales demos are pretty high-touch, which means they should be reserved for customers who are going to pay you enough to be worth it.
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.
Check out my new book, The SaaS Playbook, for more on how to build a multimillion dollar startup without venture capital.
And if you want to dive deeper into sales demos, I recommend the book Product Demos That Sell: How to Deliver Winning SaaS Demos by Steli Efti.
I love customization hacks like this, and want to do more of them for Indie Hackers.
For example, right now we're surveying people who join to find out where they are in their journey, what their interests are, etc., but we're not doing anything with that information. Everyone gets the same Indie Hackers no matter what they select.
I agree this hack is actually brilliant and very parallel to how a lot of other things happen. Just like the very example in this article of the Access Database and Email solution that was hacked together is good when you're a small company and don't have resources to create a solution, but once you grow and that solution doesn't scale you have to address it differently.
Maybe an odd question @robwalling but do you have any suggestions for ways to help solo founders workout the "sales muscle" besides just doing lots of it? Like is there anything you did in your personal life early in your career to become more comfortable in your own skin and gain confidence to help your salesmanship? 9 years ago you and mike taber were the reason I was inspired to learn to code btw so thanks for the content!
I’ve seen folks do a few things to get more comfortable with sales:
Listen to recorded sales calls. I’m not sure if you can find some online, but I’d bet if you asked here on IH or in MicroConf Connect you could find someone who would share a few calls with you.
Do a role play with a team member or friend. This is if you’re very early and still stressing about talking to unfamiliar people.
Hone your pitch at in-person events. I went to a conference where I had to explain what Drip did about 100 times and that got me way more comfortable with talking to people about it. I wasn’t selling the software, just explaining what it was and how it worked helped break down some mental barriers I had around talking to people about the product.
And, of course, doing sales demos :-) In the early days you’ll need to give a lot of them, even to unqualified prospects, just to learn how people think about your product, and to improve your interpersonal skills.
Thanks so much for the tips. I really appreciate you taking the time to respond! I think some roleplay sales is my first step. Hopefully I can say hey one day at a microconf
Thanks for this quick tips, Rob.
As an introverted-creator, I dread talking to people.
Seems like these steps could help me prepare for it.
Loved your book, already rereading it <3
These are great tips, especially for the modern way of doing sales. Less of trying to be pushy and be more focused on giving / asking for info.
How did you get those first few sales demos when you were growing?
I tend to be good at inbound marketing so I used content, SEO, appearing on podcasts, and working my network to get early demos.
Honestly, going to my network with direct, warm emails was a big driver in the early days (“I know you use XYZ-ESP, here’s how we’re better. If you’d consider a switch let’s chat!”).
Great post as always,
The hack to lower sales effort by redirecting prospects based on value metrics is a smart way to optimize resources. Overall, a comprehensive guide for founders navigating the sales landscape! 🌟
Thank you for the detailed deep dive, Rob!
Awesome insights. I've also been trying to start my own SaaS even though I don't have many years of experience with building software. I feel like the scariest part of building something is coming up with a bad idea and building it out and having nobody use it.
Thanks Rob!
Have you been able to measure a difference of conversion rate for same-size prospects before and after you changed the threshold between screencast and in-person demo?
Yes, we closed 2-3x more sales when we did demos. But keep in mind, if you are selling to cheap or unqualified prospects, then closing more of them doesn’t help your business because they churn out quickly.
Reeeally interesting article, Rob, thanks! We recently bought your book "Start Small, Stay Small", and using it to launch a SaaS (which we've internally used for ≈ 1 year, too slow, we know haha).
Solid article, Rob. Thanks for the overview.
What lead nurturing techniques did you use, if any?
Almost solely email sequences.
Good stuff. Also found your website. Bundling the books based on content type is genius.
Looking forward to the read. cheers
rob giving the best advice as usual. I book marked it and saved it to Google Keep for future use.
The number 1 I took from this was the educate don't sell quote, gonna focus on that.
Also, the whole start at a lower price and talk to whoever and whenever you can to learn as much about the market as possible.
Hi Rob, thanks for the great article. I also just bought your book and I'm excited to read it ;)
Awesome, glad to hear it! I hope you enjoy the book.
I hope it will give me some ideas for my current situation. I‘m building https://podcut.io/ and while I think (and have partly validated) that is definitely provides value to my users, it‘s been rather difficult to market compared to my last product. While it‘s definitely a topic too large to get into here, I‘d appreciate any kind of tiny input/thoughts/suggestions!
Just listened to Peter Kazanj on your podcast and grabbed his book right away. It's been an absolute game-changer! Easily the top sales book I've come across. Highly recommend it to all SaaS beginners out there.
When I was reading his book (Founding Sales) to prep for that interview I was immediately struck by how good it was. Since then I’ve been recommending it with the same fervor you feel.
Great post @robwalling! I have a question about when it is worthy a demo or not, and maybe it is aligned with your hack for recorded video vs live demo. You mentioned something about price as well and I am curious to know what would be the price threshold, in a ballpark, that you would consider worthy of a live demo.
Ooh, this is a really good question.
For one-call closes, it depends on how much you have to pay to your sales people, and the cost of your marketing channels (i.e. cold outbound requires a higher ACV to justify). But realistically, we used to do demos for people paying us $149/mo or $199/mo, which is probably the absolute lowest end I would consider.
If you're doing cold outbound it's closer to $7500/year. And if you're going through an enterprise sales process with multiple calls, procurement, etc you need to charge $25k/year at a min, and ideally $30k and up.
HOWEVER...in the early days, I would talk with pretty much any qualified prospect because learning is your most valuable asset. At a certain point you'll see the same patterns over and over and at that point you tweak your javascript to show the pre-recorded demo to more and more people coming through as you expand your sales capacity.
Perfect! This approach really makes sense for starters or long-runners.
You just had Peter Kazanj of Founding Sales on your pod. I picked up his book, and it has been extremely helpful. Probably the best book I’ve read on sales. I can’t recommend this book enough for anyone starting a SaaS.
I know, right? It’s such a good book. I’ve started recommending it to anyone who asks me about doing sales as a founder.
Great list. Another tactic I would add to #1 is storytelling. If you can connect with your customer through your own stories, or other customers stories, and really bring to life the problem that you're solving; it's way easier, cognitively, for them to see themselves solving their problems with your product.
Hey @robwalling, under "Ask the right questions" you have several questions that really reminded me of the JTBD (job-to-be-done) framework. Was this your inspiration for this particular section?
JTBD definitely influenced us as we developed our sales process. We started with our own questions based on gut instinct (this was 2013/2014 so before JTBD had become so popular). Then we massaged the questions over time as we learned more about how others were doing this.
Yeah, this has been one of my biggest learnings as I learn how to sell. At first, I wanted to talk to anyone who would speak to me, but it's a waste of everyone's time. Worse, it even resulted in me building features that nobody (except someone who never became a customer) wanted.
@robwalling so you're saying that if they're a 'yes' at the end of the call, you create an account for them on the spot and input their CC details for them? That's a cool move. Does anyone ever take you up on it? For me, it'd be rare for someone to be ready to pay then and there.
And what's the process — they stay on the call while you ask them for their info and you input it manually through your backend, then send them a temporary password?
Yep, I've actually done it two ways. At one point we would just create a free trial account for the prospect and let them enter their CC info, then we started offering to take their info over the phone and we would just enter it into the payments screen on their account as any other user would. Some folks would do it and some folks would decline, but we'd still turn the account over to them in either case.
For the password we'd typically ask them to click "forgot password" so they'd get a reset email. If I had less technical users I would do that for them.
Love this, thanks for sharing @robwalling! When does your new book come out?
Thank you!
The Kickstarter hardcovers should start shipping next week from the fulfillment house. Paperbacks ordered from saasplaybook.com will go out a week or two later, and it will be up on Amazon/Audible a couple weeks after that.
How did you get the audio for your book? Did you read it aloud yourself, or hire someone else to do it? Or is there some new AI tool for this
I read it myself. The AI we have access to as consumers is still not close to replicating individual voices.
Excited for it! I should be getting a couple of copies in my mailbox ☺️
❤️❤️
Yeah super 🚀 -- Qualifying leads is key, not all are equal, but all can be valuable, for different use cases.
Great post as always.
Nice bunch of tips ! Thank you
Hey Rob, I agree that your insights on the SaaS sales process at Drip are truly enlightening. I also appreciate the focus on educating rather than hard selling and qualifying prospects before demos, which aligns perfectly with the modern sales ethos. This approach of nurturing relationships rather than pushing for immediate conversions is a valuable takeaway for any business. Luckily, I found another informative resource on how to clear system storage on Mac here- https://setapp.com/how-to/how-to-clear-system-storage-on-mac It provides practical tips that can help streamline operations, much like your sales strategies streamline the customer journey. Anyway, I hope this post will be helpful for anyone looking to enhance their SaaS business sales and trust. Thank you!
educating is best. easiest way to create trust and eventually sell. great read.
Good one I like the A hack to lower sales effort
How did you adapt your sales process as Drip grew?
Thanks for sharing. When I develop my own products, I also put myself in the user's shoes and use my own product. When explaining the product to users, I also use empathy to explain, because users are not familiar with the product design process.
Really interesting post - What would be your recommandation when launching a micro-saas that brings a new tech to a quite saturated market ?
Really a great post - thanks for sharing.
We recently launched our SaaS solution and now doing a lot of demos. I am happy to hear (in the end of your post) that you in the beginning took all demos (To get as much feedback from the market as possible) and then over time you graduatly screened the potential customers to optimize your demos/sales resources.
We are taking the same approach and the input in your post is really helpful for us - appreciated👍
Can you maybe share how you approached getting the leads / demo bookings? How did you attract potential customers/leads? Google adwords, cold calling, Capterra?
Could be interesting to hear and also your experience on does/donts in this field.
Thanks
Thanks for sharing - absolutely agree.
Sales is about building a relationship, earn trust and help them solve their problems.
& if you focus on transformational outcome rather than transactional only, i guess it will play out for you on the long term :-)
It's good to be a hacker... but at first place, a sales hacker
Thanks for sharing this
Love the hack about booking a demo
@fastsociety We will have to discuss our lead qualification strategy in future as we learn and grow
Thanks for sharing Rob! Funny I read this today, I was just doing research on new sales calls tactics yesterday.
One thing I'd add is that prospects are now used to sales calls starting with questions, but they just want to see the demo. It's important to make them feel like their time isn't being wasted, and they don't become impatient.
here are a few notes I'll add to what you have:
Hope this helps whoever is looking for more sales advice.
Thanks for sharing! Great additional inspiration.
thank you for sharing this Rob!
How many were you at Drip? Would be interesting to know if you implemented this approach from the beginning or later with more resources–eg who was doing sales and demos? Was the same dev team in charge of both dev and sales or there was a split of roles?
How did you generate more leads?
Great read and insights. Coming from a sales background, taking this consultative approach pays dividends, especially for long-term customer trust.
In short, make it about them and not you or your company, product etc. Develop an emotional connection through showing concern towards a problem they are facing and one which you can solve.
You truly have been an inspiration to me Rob, ever since 2010 when I read "Start Small Stay Small"
Amazing. Glad to have been part of your journey. 🚀
That pop up idea is wonderful, so easy to make demos nowadays with products like Loom or Vidyard. How did you structure your demos? I know for some doing a demo and asking discovery questions can quickly turn into word salad, interested to hear how you structured your calls.
I love your advices explained in this thread. Another great tip I would like to add for growing Saas business is to user feedback and retention.
If you can't convert your existing customer into a retention customer, you are already losing the business
Woah, I did NOT realize I was doing sales demos all wrong! 😱 This is a total game changer.
I used to think demos were just boring product tours. Now I see they should be like Oprah - ask questions, listen more than talk, and focus on solving problems rather than features. 💡🗣️
My favorite tips: qualify leads BEFORE the demo to avoid time wasters, and follow up relentlessly until you get a hard yes/no. No more crossing my fingers they'll come back! 🤞👋
Also love the genius pop-up hack to redirect low-value prospects to a video demo. Save the hand holding for big fishies! 🐟🎣
This advice just revolutionized my sales strategy. So helpful! Who's with me in leveling up their demo game? Share the most valuable tip that clicked for you! 👇🙌
Thanks for sharing your experience and tips, Rob! I'll definitely be implementing some of these strategies in my own startup.
Thanks, Rob. Lots of good points about sales. I like this especially,
"If the customer is not fit, be confident & polite to say no and move on. That is better than a churn after 2 months"
Nice tipps @robwalling, would you be interested to act as mentor for a rising saas?
I appreciate the offer, but I am fully booked advising my current investments.
Thanks for sharing this.
Valuable insights, thanks for sharing!
Great insights, thanks for sharing.
Very useful budy
Do you advice to use third party website to sell you Saas or just go pitching to potential buyers? How do you go about that
This is valuable ! I have built my product but I don't know how to land my very first client !
This article on SaaS growth and sales demos is a gem! Thanks Rob!
It's brilliantly written for folks like me who aren't sales experts. As I grow my app - YVisuals.app, I realize the importance of educating rather than just selling in our email campaigns. It's the game-changer.
Here's hoping we'll have the energy to run more successful campaigns and convert our free users into paid customers. Wish us luck on our journey!
These are great tips, thank you! I've curious about the idea of offering a free option as a trial. Do you think this is a good idea, or are demos with upfront monetary requests a better option?
Really depends on your price point and how your customers want to buy. Surprising to most of us developers/makers, most customers want a demo of software they are considering. But it doesn’t always make financial sense to do so (I had another answer in this thread about price points where it makes sense).
Free trial vs. not, demo vs. self-serve, CC upfront vs. not, freemium vs not…all complex questions with many variables. I have a few rules of thumb in my book (saasplaybook.com), and usually I recommend starting with those and then re-evaluating as you learn about your specific market.
nice tips I still cannot follow cause I am too lazy
You're the man Rob