The Complete Blueprint to B2B SaaS Sales Conversions

Casey Hill

Although not all SaaS companies have robust sales teams, data from SaaSx shows that the majority of SaaS teams with over $2.5 million in ARR (Annual Recurring Revenue) use sales as their primary driver of growth. Especially for businesses selling mid-market or enterprise solutions, having experts who can demo and explain the software in-depth is vital.

This handy guide reveals the 3 major hurdles B2B SaaS sales teams face, and explains step-by-step how to overcome them to quickly scale your growth. We'll focus on:

SaaS Sales Hurdle #1: Demo No Shows

SaaS Sales Hurdle #2: Leads “Going Dark”

SaaS Sales Hurdle #3: New Users Getting Stuck in Trial

OK, let's break this down, and get your B2B SaaS growth flying again!

SaaS Sales Hurdle #1: Demo No Shows

Many SaaS organizations offer the ability for interested prospects to book a demo online at the click of a button. This is important, especially for more complex products, but demo no-shows are on the rise. SaaS companies typically contend with an average of 10-20% demo no-show rates and that can have a critical impact on sales and quotas. Below are the most common reasons we see for prospects not showing up and our recommended solutions. 

Time Zones:

A common reason for no-shows is contacts think the meeting is at a different time. It could be a miscommunication through your scheduling system, it could be they misread it, but whatever it is, they didn’t show up at the slated time, and that is frustrating for both you and them.

Solution: The way to fix this one is just clarity. Make sure you follow-up and state the specific time and date of the meeting. One strategy is right after a customer books, you can send them a personal video that clarifies the meeting time and puts a human face to the meeting. See this example:

When Ontraport implemented this strategy they reduced their no-show rate by 15%. Another strategy here is to have detailed automated reminders that fire out the day before the meeting. Calendly reports that this reduces demo no-show rates by up to 28%! It’s important to not wait until just a few hours before because if the time zones are dramatically different (for international clients for instance) the meeting may have already misfired. 

Purpose and Value:

Another common reason that people miss demos is because they are uncertain of exactly what is going to happen. Is this an automated demo that is being emailed to them? If it’s with a rep is this just someone who is going to try and sell them? Will the rep they meet have the experience necessary to understand their complex set-up?

Solution: There are a few things to do for this one. First off, start with a good copy on the website. When someone clicks the booking CTA, don’t just take them to a calendar. Have a blurb that explains how one of your company's experts is going to add value to them, speak to their pain points and digest their business needs. Avoid the phrase “Sales demo” or “Sales call”. Instapages has a series of great, high converting demo pages that I encourage you to read through.

But to pull away one good example:

This page clearly lets the prospect know what they can expect with the copy on the left and preemptively addresses some of their likely pain points. 

The next important piece is to clarify if this is an automated demo or an in-person. Most people will assume that if they book on a calendar it’s an in-person demo, but not everyone. Make a subtle comment one way or another,

“One of our experts will guide you through…”


“With this easy to navigate, self-serve demonstration, you will be able to see all the benefits of…”

Both styles of demonstrations can have value, but you want to make sure there isn’t misunderstanding about which the prospect is getting. 

Finally, prospects love to know that the person they are talking with is competent and expert in their specific needs. Let’s say you sell a SaaS product that sells to charities, other SaaS companies and financial institutions. If you ask them on the initial opt-in form their industry you can follow up with a personal email (or personal video email) after the booking and state,

“Hey this is John from Company ABC. I am one of our team's experts in financial institutions (I spent 10 years with Goldman Sachs before I joined Company ABC). I am excited to navigate you through the platform….”

That establishes your authority and builds trust around the ability to deliver value. If they think they are getting an industry expert vs. a sales rep, they are less likely to brush the meeting off.

Too far out:

If a meeting is more than 7 days out the no-show rates increase dramatically. 

Solution: The answer to this one is pretty basic. Follow-up frequently. Until you get a confirmation, follow-up every 3 days until the meeting. Even once you get a confirmation, still make sure to follow-up the day before. Oftentimes companies who are prospecting a solution and book lots of different meetings, end up losing interest in that area, or it was just an early stage looking or they went with a competitor or they simply didn’t plan that far in advance. Follow-up will be the key to reducing no-shows from this. 

Client needs/Emergencies:

Prospects who miss a call will commonly note that an urgent business need arose or a personal emergency cropped up. 

Solution: There is of course some percentage of missed demo meetings that are inevitable. Emergencies will happen. How you follow up, on the other hand, may determine if they rebook. 

When someone has to reschedule, always be empathetic and yet re-iterate the value of the meeting,

“Hey Sara, I am so sorry to hear about the emergency vet visit for Bernie. If you send me your address I would love to send the little guy a toy for his recovery. 

As for our meeting, I am still excited to navigate you through how we can save you a mountain of time with your accounting. This is a use case of a similar business: [link usecase] if you want to check that out before our next call.

Rebook any time that works for you: [insert calendar link].”

SaaS Sales Hurdle #2: Leads “Going Dark”

The meeting just went amazing. The decision maker was on the call and they were loving what you were putting down. At one point they even said the words, “Wow, yeah that’s perfect”.

You hang up and shoot a wry grin at your co-worker sitting next to you as you blow the steam off your imaginary finger gun, “Sealed and done” you say like you're a sharp-shooting badass.

Then they go dark and you never hear from them again. A story nearly any sales agent can relate to.

But why does it happen? Why do good prospects disappear suddenly?

Solution seems valuable, but there isn’t urgency:

Oftentimes the prospect you were chatting with genuinely liked what they saw. But at the end of the day they are not completely won-over in terms of how easy it would be to set up, if they would get those same results or if they want to invest the time in learning this new thing and making it work. It seems nice but things are going okay without it. It’s not a crisis situation.

Solution: As the sales agent, you need to skillfully paint the before and after, and the path to get there. Use as much directly applicable content as you can (usecases, testimonials etc.) to portray exactly how similar businesses got certain results. Don’t send them a follow-up that just says,

“Hey Carl,

Just checking in to see if you got my proposal.


Lame generic person”

Instead, shoot them a follow-up that says,

“Hey Carl,

Thanks again for your time last Friday. So I wanted to send over a few more resources that I think will help. First off, I know a lot of our conversation centered around how to get the team to adopt this new tech stack. Let’s be honest, that is always one of the biggest hurdles in making a software switch.

Here are some detailed use cases on how some other fin-tech companies made the switch (and saved over $300,000 in man-hours): [insert usecase]. Especially for your team, the section around compliance on page 6 I think will be a game changer. When your reps see how much manual task reduction this is going to bring them, I think they will be pleased. 

Also, I wanted to send you our onboarding/roll-out plan (attached below). If you were to come onboard, this guide takes you through all the support you will receive from me, our technical reps and our migration specialist. We definitely are in your corner the whole way.

Look forward to hearing back (and hope you enjoyed the weekend fishing trip!).


Casey H.”

In the second message, you present new value (use-cases), you address the context of your old conversation and the major reservation that they had (migration complexity/team buy-in). You include a specific number around their savings so they have that floating in their heads. Who doesn’t want to save $300,000?! You are relatable and don’t sound robotic. This will substantially increase your likelihood of them buying into the solution. 

Lack of cross-team company buy-in:

The prospect you talked with loved it, but another decision maker is less thrilled. They think it seems like a lot of work and unnecessary costs. They don’t want to retrain their team. They are taking the prospect’s excitement and dousing it with a bucket of water.

Solution: You need to understand the organizational structure of the companies you sell into. If this decision requires both sales, marketing and legal to all be on the same page, then you need to have a specific value and pain-point reduction plan for each department. 

Maybe you almost entirely talk with sales and marketing folks on those front-end demos but legal needs to buy-off. Well, then you need to have specific collateral for them! In a follow-up email, send the prospect not just information that helps their department adopt your product but use cases/collateral that helps them sell it to their team. 

The rest of the team hasn’t talked to you. The prospect can’t explain things to them, after 1 demo call, nearly as well as you can. So give them the collateral they need to win. 

Your competitor won them over:

Look, sometimes people are really excited but then they see something that excited them more. Or maybe a competitor bashed you and they had a change of heart. Or maybe they were lured in by a, “if you buy this week!” type of offer. 

Solution: You can’t win them all. That is okay. What you do here is thank them for their time, let them know if things don’t work out you would love to help and set 11 months out as a task follow-up in your CRM so when it comes annual renewal time, you can possibly intercept them if they are having problems.

It was an early evaluation:

Sometimes the prospect is excited and energized to see a possible solution to one of their problems, but they are still way out from making the decision. 

Solution: Sales cycles can be long. Below is the ideal number of touch points for a SaaS closes:

The full article and video are here:

But essentially you are looking at between 5 touch points (SMBs) to 13 (enterprise) to close a deal. Enterprise sales cycles can be upwards of 6 months. So the point is, maybe it was just early. Don’t stop trying. Keep sounding valuable insights and collateral and if they go dark for more than a few weeks, switch them to an automated email campaign (that way you stay on their radar). 

Your value pitch isn’t strong enough to overcome switching pain:

A prospect can be interested in a few things they see but then go back and think, “Yeah this is nice but it’s going to be such a pain to switch over X, Y and Z. It’s just not worth it”.

Solution: Switching from an existing system or an existing process is hard. It’s a huge time commitment, you worry about downtime or disruption to new customers (or existing customers) and there is a lot of uncertainty around it. Your job here is to show them how you will help make it painless.

Give them specifics! Make commitments.

“Hey Sara,

Just touching base after our last meet. I know one of your chief concerns was just all the effort and work that goes into switching from your existing systems. I wanted to take a moment to tell you a bit more about how we help.

First off, we have done this thousands of times before. We know exactly how to get data migrated and switched over quick and we will have our team helping you throughout the whole process. Typically the whole switch takes no more than 2-3 weeks, but we personally guarantee it in 4 weeks. If it takes longer, you don’t pay until it’s ready. 

Here is a video that walks through the exact process and what we would need on your end: [insert video explainer]. After it’s all said and done, we see a median task reduction time of 28.7% (based on over 3,000 customers polled).

I know changing things is a hassle, but wanted you to be aware of how we have your back. 


Casey H.”

Here we address the pain point head on. We provide a guarantee so they know exactly what to expect (things being stuck in limbo is their worst nightmare). Then we bring them back to the value we are bringing to the table by reminding them of the benefit (task time reduction) and couching it in data from customers.

Finally, we empathize with the fact that this process is a total headache. Don’t forget to be human, at each point in the process.

SaaS Sales Hurdle #3: New Users Getting Stuck in Trial

The majority of SaaS companies today have some sort of trial. It might be a free trial with reduced features, or even a paid trial. But the customer isn’t in contract yet, and they are still essentially a lead. These customers, however, are interested enough to hop into a trial, so they are your best opportunities!

Let’s look at why they get stuck and what you can do about it.

They never (or barely) use it:

The number one reason that trials tend to fall off (especially free trials) is that people hop in with no commitment, and then either forget to use it, or use one aspect of it, hit a roadblock and just decide it’s not worth their time.

Solution: This is actually a complex and important one.

First off, you want to try and make sure you're not losing people with a bad UX (User Experience). The name of the game when it comes to trials is simplicity. You need to guide them through the experience. Gather as much information as you can (softwares like Pendo can help you get great data here) and try and validate the process with testers from the outside who you can riddle with questions. A small bug or UX/UI confusion can cause you to lose a lot of business so be diligent here.

It’s also important to look for clear trends here and discernible milestones that lead to conversion. For instance maybe you find that people that activate something in their accounts or do X amount of a certain thing usually convert. That gives you direction to try and try and encourage people to get through those things.

An overlooked, but unfortunately common problem, is they never activate their account! They sign-up and the activation email hits promos or spam and that's the end of things. To address this make sure your automated set-up emails are set to be “transactional” and if you are still having issues consult an outside postmaster. 

Another issue is no urgency. They were passively interested but they needed that extra push to get moving. Check out this great follow-up email from Sleeknote,

What the email does a good job of is addressing the value they are missing (converting more leads) and exactly what to do next. That second part is a commonly missed one. Don’t just encourage them to “Get Started”. Encourage them to do something very specific, like Sleeknotes' example of implementing your tracking code.

This is also a great opportunity to use a personal video email to onboard new trial users. Unlike plain text emails, personal video is able to leverage facial expression, tone and body language. The free trial, after watching that video, almost immediately will feel more invested in the decision as you, the company, have chosen to invest time in them (in the world of automation, people are shocked when you take the time to do something personal). 

Here's a great example from the team at Design Pickle:

They use it, but they don’t get a result:

They get in and they use your product a bit but because they can’t see the dollar sign difference, they hold off on the financial commitment.

Solution: You need to help them see a tangible result in the trial. Plain and simple. Your team needs to be engaged, trying to hop on 1:1 calls with them or sending them the right resources they need to generate a result. This is a critical component of a trial. 

Part of the solution is you want your team to have a clear sense of their goals. This is done by having effective discovery done during the initial 1:1 demo phase. If you are a more hands-off or self-serve product, you should ask the relevant questions via the trial sign-up form.

Whatever direction you take it, you need to know their pain points and goals, so you can be working to get them there. Remind them about the features that directly relate to these goals. 

Also make sure you have a data informed and robust onboarding process. They might have used it, but still be missing out on key aspects of it (hence why they missed their result). 


They like the product, but are worried about the time for a full implementation:

Often time with trials people will poke around a bit, test a few things but aren’t implementing the full thing. This can often lead to a stalemate where they are interested, but not completely sold yet.

Solution: If a customer is worried about the time to implement the solution you need to lay it out, clear as day, about how you are going to help make this process painless. Don’t use generic phrases like, “Our customers tell us getting set up is easy!” or “Most customers are up and running quick!”.

Give them hard numbers and facts and an exact blueprint and roadmap of how they will be implemented. Make sure they know how your support works to help them. Make sure they know why your team is going to be next level advocates in their corner. 

After the close

While this article has touched on how to improve your SaaS close, remember that is just the tip of the iceberg.

The world of SaaS circles around recurring revenue and CLTV (Customer Lifetime Value). You have to keep winning your customer over, month after month. It never ends).

At a core level, it is critical to remember that effective SaaS sales (and SaaS retention) are about providing clarity, simplicity and human connection throughout the journey with your company. People will buy and stick around if you solve their pain points, make it easy and build relationships. Sometimes SaaS can seem deeply complicated but the reality is…. it’s as simple at that. 

About the author
Casey Hill
Growth Manager
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