4 Recent Lessons I Learned About Improving AiSDR’s GTM Strategy

Executing a go-to-market strategy is never without its challenges as even the best-laid plans can and will hit some snags along the way.

Through trial and error, I’ve learned a lot about what works and what doesn’t for AiSDR. And these lessons have been key in refining AiSDR’s GTM approach and guiding my team in the right direction.

Here are four important lessons I’ve learned since running different AiSDR GTM plays.

Resist the temptation of offering free trials and pilots

Free trials and pilots may seem like a great way to get customers on board, but they often create more problems than solutions.

In my experience, there are two situations where free trials work:

1. Your product delivers clear, immediate value.
2. You need early users who can test and “break” your product so you can work out kinks and identify features people want.

If you don’t fall into either camp, you’re likely destined for one of two disappointing outcomes.

The first is that many people simply don’t use the trial. They sign up with good intentions and the desire to use it, but they never make the time to properly explore your product. They then let the trial period expire, leaving you with nothing except a dead lead.

The second, and arguably more concerning issue, is that users who blindly use your product will leave unsatisfied. They stumble through features, fail to realize their true value, and leave frustrated after the trial ends. They’re convinced your product either (a) doesn’t work or (b) doesn’t work for them, even though they didn’t experience it properly.

What I do instead

Instead of free trials, I’ve learned to offer paid pilots with dedicated customer success and GTM engineers.

While this might seem counterintuitive, especially for early-stage companies, paid pilots offer several benefits.

Customers who pay (even if it’s a reduced pilot fee) are more committed to seeing the product work. Throw in a GTM engineer dedicated to customer success and target milestones, and you’ve got a recipe for results.

A well-structured paid pilot shows you’re confident in your solution, committed to their success, and ensures that customers:

• Have skin in the game and are motivated to use your product
• Get proper guidance and support
• Understand your solution’s full value
• See tangible progress towards meaningful milestones and results

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Don’t offer “one month free” to reduce churn

When fighting to reduce churn, it’s tempting to offer customers a free month to change their minds.

But this last-ditch effort works as well as a Hail Mary at the end of a game. 

And in the end, you waste time and money.

Here’s the cold, hard truth.

By the time customers reach the cancellation screen, they’ve already decided your product isn’t for them.

In other words, they’re already checked out. And offering a free month is like putting a band-aid on a broken arm. It doesn’t address the real issue.

Here’s what typically happens: The customer accepts the free month (who wouldn’t want something for free?), but rarely uses your product during the “free” period. And when the month ends, they still cancel.

And you’re left with the sunk cost of providing your solution and supporting a customer who was already out the door.

What I do instead

A better strategy to reducing churn before it happens is to focus intensely on delivering value within the first month of the subscription.

Since the customer’s already paid, they have a vested interest in seeing results.

In our case, this means getting actual meetings booked for customers through AiSDR. The more meetings booked, the more value customers see. As a result, they stick around because they want to, not because you charmed them with a free month.

Don’t offer to “pause” subscriptions

Pausing subscriptions sounds like another customer-friendly way to retain users who need a temporary break, whether it’s due to the holidays, a slow summer season, or other reasons.

But after trying it out and running the numbers, I’ve discovered it’s a lose-lose for everyone.

Here’s what typically happens: Customers hit the pause button, thinking they’ll be back, but they often never return. And if they do, it’s because you charged a small maintenance fee to keep things running, making them annoyed or frustrated by unexpected charges. 

On the other hand, if you pause subscriptions for free, their account sits in limbo – not active, but not fully canceled.

Meanwhile, you’re still incurring the costs of maintaining their account, send notifications, and keep the infrastructure running. All for customers who are unlikely to reactivate.

What I do instead

There’s an easier solution than pausing the subscription.

You handle it like a regular cancellation.

Just like when you cancel your Netflix subscription for a month if you know you won’t have time to watch anything, you have customers cancel their subscription entirely. If they want to return later, they can just sign up again.

This approach has several benefits:

• No risk or guilt of indefinite pauses for customers
• Your monthly recurring revenue is crystal clear with no ambiguity about paused accounts
• You’re not paying infrastructure costs for inactive users
• The re-subscription process is straightforward for returning customers
• You and your customers enjoy clarity and a clean break

And if you want to win back customers, you can give them a sneak peek into your product roadmap. Especially if you have any features on the roadmap that they’re super excited about.

Bill in advance every time you can

Here’s a critical lesson about cash flow that too many startups learn the hard way. 

Whenever possible, bill your customers in advance via credit card.

This simple practice will make a massive difference in your company’s financial health.

Many companies, especially ones flush with VC funding, get comfortable with billing customers after delivering services.

This can create an illusion where they see strong revenue numbers on paper, yet in reality they’re burning through their runway.

If you think about it, billing after delivering is like giving your customers an interest-free loan. You’re covering all the costs, only to wait 1-3 months to get paid. Worse yet, you assume all the risk if the customer disappears and ghosts you.

I’ve seen too many VC-backed companies ignore this until it’s too late and they hit a cash crunch.  

What I do instead

Even well-funded startups can run into trouble if they don’t manage their cash flow properly.

Here are some of the advantages of billing customers before delivering services:

• You have real cash in the bank to fund operations 
• Your revenue reflects actual money in the bank, not promises to pay
• Your investors have a clear picture of your company’s health
• You avoid the headache of chasing down late payments
• You reduce the risk of non-payment

By billing in advance via credit card, you protect your business and ensure a healthier financial future.