6 Lessons Learned from 6 Years of Founder-Led Sales

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In 2017, with the help of my brother, I started my first company – AXDRAFT. Its objective was to help companies automate their legal documents and improve their contract management. We also launched a separate service called Avodocs, which provided free legal documents for startups.

Then near the end of 2020, I sold AXDRAFT to a larger legal tech corporation called Onit. For another three years, I worked for Onit as a general manager of AXDRAFT.

A few months ago, my internal entrepreneurial spirit started to burn again, leading me to start my new company – AiSDR. Our goal is to launch AI-powered tools that will help generate company growth.

Over these past six years, I’ve had the opportunity to experience many different kinds of B2B SaaS sales:

  • Enterprise
  • Mid-market
  • SME
  • Pre-seed
  • Startups in the process of series A / B / C

I’ve also taken part in pricing experimentation (from as low as $900 per year to as high as $200K), as well as cold outbound prospecting and building high inbound flow processes. On my own, I reached $2M ARR, and I played a role in $10M and $100M ARR companies.

My path saw its fair share of hurdles and stumbling blocks. Whether it was the COVID-19 pandemic or the current war in Ukraine, I quickly came to realize that it’s hard to prepare for everything. Yet at the same time, the more you invest in your own abilities and preparations, the more prepared you’ll be to weather and navigate any possible storms.

To that end, here are 6 lessons I learned during my time in founder-led sales. 

Lesson 1: Focus on inbound early

In my eyes, this is probably the most important lesson to take away. At AXDRAFT, we started to invest in inbound after having been on the market for 2.5 years. It still took us about a year to get everything set up and start producing consistently good results.

Once our inbound efforts built some momentum, we began to see a predictable lead flow of interested customers who would close 2-3 times faster than outbound leads. 

Going “outbound only” for three years made sales an uphill battle, and if I could do it again, I would have integrated inbound from Day 1.

What you can do 

Here are some steps you can take to start building your early inbound:

  • Create a website with a waitlist as soon as you have an idea
  • Launch the website, along with a description of value props and unique selling points
  • Include early mock-ups of what your product might look like (Figma helps a lot here)
  • Spread the website on as many platforms as possible 
  • Start creating content ASAP (blogs and social media are good early options)

I took many of these steps with AiSDR, and I managed to get 130 companies on my waitlist within a month. Not only are other businesses an amazing source of feedback, but many of them are set to become early customers.

Speaking of which, if you want to stay up to date on product news or be one of the first to use AiSDR, feel free to join our waitlist.

Lesson 2: Outbound is about quality AND quantity

Outbound is hard. It’s no stretch of the imagination to get zero results after sending 100 emails. If anything, you can make a case that it’s the expected outcome.

Once you’ve sent 1,000 emails, you might start seeing some predictable conversions. And if you’re scoring a response rate of 8-10%, you’re doing pretty well. However, to be blunt, only 20% of those responses are likely to be positive.

Crafting multi-touch sequences across various channels can improve conversion, but there’s no direct relation between the number of steps in a sequence and the conversion rate. In my experience, 5-7 step sequences via email and LinkedIn often performed better than 15 or 20-step sequences that included cold calls.

Still, there’s no one-size-fits-all solution. You’ll have to experiment and figure out what works best for you and your target audience.

What you can do

There are some tactics you can employ to boost your chances of success in outbound:

  • Know your ideal customer profile as well as possible (who they are, their pains, how you solve them, which customer stories are most relevant, and which channels they use to communicate)
  • Get your hands on good data (specifically, meaningful qualification criteria beyond what ZoomInfo has to offer)
  • Relentlessly execute your strategy

To give you a clearer picture as to the difficulty of outbound, I’ll share with you some of what I’ve learned from SDR leaders of several top companies.

They run SDR teams of 15-20 people, and each person has a monthly quota of 6-10 meetings. This might not sound like many, but only 15% of SDRs met their quota. In the end, the revenue generated from meetings booked typically matched the money spent on the SDR team. So while you’re not losing, you’re not exactly winning either. 

Lesson 3: The fastest bird gets the worm

Here’s a general rule of thumb: Time kills deals. You must engage leads while you’re still fresh in their mind. If you can respond to an engaged lead within 5 minutes, you can improve conversion by up to 50%.

I’ve validated this fact many times on my own, and through conversations with other founders.

When I was at AXDRAFT, my ability to immediately respond to an email from a lead at Walmart (even though it was 11 PM) was what eventually led to our landing a contract with them.

At AiSDR, 80% of waitlist sign-ups that I’m able to respond to in 5 minutes convert into a meeting, but only 20% if I respond slower than 5 minutes. Interestingly, auto-reply using HubSpot or something similar doesn’t seem to work. I think there’s something special about a non-marketing response that’s also personalized.

Lesson 4: People respond better to founders

Let’s consider email campaigns for a moment: People seem to be 20-30% more willing to open emails from founders than emails from SDRs, even if it wasn’t written by the founder. So even if you’ve grown beyond being a founder doing sales outreach, it’s still a good idea to run some campaigns under the founder’s name.

If you can, it’s also wise to leverage your connections or expanded networks. For instance, you’ll have a much better chance of landing a meeting if you reach out as a YC founder for expert advice. Or if you attended a prestigious university or worked at a famous organization, you might be able to connect and set something up with alumni.

Even if they don’t buy anything, you should approach conversations with the goal of learning about your target audience’s processes, needs, and opportunities to use your product to solve their pains. Who knows? If your product solves their pains, the conversation can rapidly lead to a sale. This is how AXDRAFT closed its first 10 contracts.

Lesson 5: Be respectful to leads (even if they don’t buy your product)

This is sometimes overlooked, but maintaining a kind, friendly, and genuinely helpful approach can open up a lot of doors for you, especially in the early days.

When AXDRAFT was accepted into YC, I began reaching out to people for product feedback. Eventually, I scored a meeting with the then-Head of Legal Ops at Twitter.

Twitter didn’t have a problem that we could help solve, but since I knew the market well, I suggested a few products that could address their challenges. 

Some time later, I followed up and asked if my advice turned out to be helpful. As it turns out, it was, and Twitter’s Head of Legal Ops introduced me to the Head of Legal Ops at Slack, who did have an issue we could solve.

After several discussions, Slack became our first US customer. And they in turn introduced us to Vimeo. Next thing you know, we had several customer logos we could use to help scale our sales.

Keep in mind though that not every prospect is a good fit. You’ll have to learn to recognize which ones are, and move on if they aren’t. But if you’re respectful and helpful to your prospects, you may be able to leverage those contacts and ask for introductions.

Lesson 6: $10K and $100K contracts take big companies the same time to approve

This is a fact of business that you should internalize. Large companies are comprised of layers upon layers of processes: procurement, security review, legal review, and so on.

My early $6K contract with Slack took the same six months as a $100K contract with a different legal tech provider they were working with at the same time.

This insight gives you the freedom to try a couple of options:

  • Don’t try selling at all to large companies (especially early on)
  • Pitch $100K+ offers to large companies
  • Find a product-led growth strategy that allows employees of large companies to sign up for your product individually, then once you’ve got many, pitch a $100K+ offer supported by a strong business case

The choice is yours.

Wrapping up

As a bonus, here are a few more quick tips I’ve learned over the years:

  • Sending follow-up messages via text or WhatsApp late in the cycle is a great way to convert
  • Don’t sell to enterprise companies without SOC-2 or some other security qualification 
  • Create an ideal customer profile early and create different value props for different profiles (i.e. don’t use a “one sequence to rule them all approach”)

Sales isn’t easy, but the lessons mentioned above have the potential to grow your annual revenue and close more deals. You may run into some bumps in the road along the way, but if you’re adaptable, you should be able to rework these takeaways into something that works for you and your business.

Lastly, finding the right tech to shoulder some of your routine work so you can focus on sales is another recipe for success. This is what we are striving to achieve at AiSDR by launching an AI-powered sales automation platform. 

If you’d like to be among those who experience how AiSDR will empower you to boost your sales campaigns, book a demo to see how it works. Or check out our blog for AI, sales, marketing, and other related content.

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