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January 4, 2023

5 DIY Growth Hacks to Juice Your Sales on a Dime

Hand juicing lemons

I firmly believe that a downturn is the time to cast your sales net deep, not wide. You should sharpen your focus and put your energy into capturing a smaller, high-quality portion of the market. This idea has buoyed the companies I’ve worked for in the past, allowing them to survive and thrive in uncertain economic environments.

Taking the lessons I’ve learned from previous downturns, I’ve compiled a quick list of 5 ways you can retool your sales and product strategies to land deals on a dime.


ABC: Always Be Closing
EBC: Everybody Be Closing

Your installed base has never been more valuable than it is now. We may be entering a period of low to no new logo growth, which means you need to protect your current customers at all costs. For a market like today, the classic Glengarry Glen Ross “Always Be Closing” should actually be “Everybody Be Closing.” You should change your mindset to think of every employee in your company as a lightweight customer success or account executive.

By everybody, I truly mean everyone in your company—the engineers, product people, and back office folks, all hopping on the phone to talk to customers. You should always stay in touch with your customers, but it’s crucial when the market is down because those are the accounts you’re most likely to grow. That’s where you’re going to land an expansion, upsell, or cross-sell. If you don’t embrace your customers right now and build deeper relationships, your competitors will.

You should always stay in touch with your customers, but it’s crucial when the market is down because those are the accounts you’re most likely to grow.

In 2015, I was working at when we hit some headwinds. Our general manager at the time told us to get in touch with every single customer. She assigned a list of top customers to everyone in the office—there were hundreds and we called every single one. Throughout those calls, we learned there were a large number of customer support issues that were unsolved; we also learned that some weren’t even logged as tickets. Using that information, we proactively dealt with each case and lowered our churn.

We also found out—this was a little bit more shocking—that most customers were only using about five percent of what we built. Some customers had been working with the product for years and didn’t even know certain features existed. After stepping in to help and show off the product features, we saw more expansions and upsells.


Apple Pie and Cookie the Pipeline

There has never been a better time to get creative on first customer contact—and get as creative as you possibly can. Every buyer is inundated by SaaS reps, who are leveraging every channel to blast their offering, which means you need to get creative when conducting your cold outreach.

One of the best examples of creativity I’ve seen happened about 10 years ago when I worked at Salesforce. A sales rep from Pluralsight spent a year sending me messages over LinkedIn. He figured out my email address, he left me voicemails and I ignored all of it. Not on purpose—I just had other things going on.

Then one day I got a call from the mailroom, telling me that I had to come retrieve a perishable item. I had no idea what they were talking about but headed down to investigate. And sure enough, when I got down there, I found a warm apple pie from a local bakery in a box with a cellophane window. In that moment, I knew exactly what was going on.

I took it upstairs and the smell of apples and cinnamon permeated the entire floor. Everyone came over to investigate.

illustration of an apple pie slice


What’s going on over here?

Can I get a slice of that?

Wow, who’s that from?

Oh, Pluralsight. Who is that?

You’re going to call them back, right?



And I did. After a series of meetings, we closed a multimillion-dollar deal with Pluralsight. Not bad for a $50 apple pie.


Welterweight PLG

Product-led growth (PLG) is a hot topic these days and for good reason—it’s a cheap way to new annual contract value (ACV). We have two of the most successful PLG stories in our own backyard, Slack and Calendly. They have taught us everything we know about PLG. They gave away nearly 100 percent of their product for free and gamified the system to attract new users. They incentivized users to share it with their network, getting other people to sign up for free causing the network to grow virally. And once the benefits have really sunk in, they go for the enterprise upsell—which is what I call pure play PLG.

Slack had the benefit of building a PLG product from day one, but most companies don’t have that privilege. In fact, if you try to jackhammer your own product to become a PLG product, it could take you quarters or years—and there’s a chance you never get there. And not all companies were designed to be PLG companies. The good news is there’s an in-between that I call Welterweight PLG. It requires a smaller investment, but still allows you to see the benefits of PLG.

If you’ve had a free trial sitting in your product backlog, now’s the time to spin it up.

A good place to start is a free trial. If you’ve had a free trial sitting in your product backlog, now’s the time to spin it up. Feature flags are a great way to get free users engaged in a trial. As the users go through the free trial, you can bring in your favorite user analytics tool (Mixpanel, Pendo, etc), and send that data to your sales team. This arms them with a greater understanding of how someone is interacting with the product and equips them to have a more meaningful, content-filled conversation when they do reach out.

On top of that, you can build a drip campaign through email, letting these prospects know the value and benefits they can get by upgrading to the enterprise version.

I currently sit on the board of a company called Connect the Dots. Connect the Dots has a product that maps your network to find the strongest connections to the people and companies you want to reach. The founders of the company wanted to build two products: PLG and enterprise. They didn’t have infinite resources—they had to pick and choose which to prioritize. They decided to put most of their effort behind the enterprise product and then worked to build a free product. Only they didn’t build the PLG flywheel, they created a lightweight version that served up most of the software functionality for free. That decision allowed them to extract a lot of the value of PLG, while avoiding the engineering and development time that takes a tremendous amount of effort.


Throw Out the Trash, and Focus on the Fresh Food

There’s never been a better time to focus on optimizing your sales pipeline. During a downturn, the way we look at our pipeline is different from every other period in history. Now is the time to focus on those top 25 percent of accounts that are most likely to close—and throw out the bottom 75 percent. Why? Because they’re probably not going to close anyway. We’ve all seen it: prospects’ budgets are frozen and they are bumping their buying decisions out to next year. That’s alright, though, because you can hone in on the deals most likely to close. You can spend more quality time with the customers that have a higher chance of success.

illustration of carrots

Way back in the early 2000s, I was a co-founder of an early-stage startup and we built a product for the healthcare industry. We had a list of 30 prospect accounts that we wanted to go after, but the twin towers had just come down and the markets were tanking. We knew buyers weren’t going to buy anything for the next year or more, so we made the decision to focus on the top five accounts and put those other 25 aside for a minute. We then put all of our energy into building highly customized demos for those five customers. We spent a massive amount of high-quality time with them and we ended up closing every single one of those five deals.

We could have gone after those other 25 accounts, but that would have risked spreading ourselves too thin. And right now, during a downturn, there is no time to spread yourself thin. You should focus on building the deepest possible relationships you can with your prospects. Full stop.

Hunt Down Old Customers in New Jobs

Why waste your time building trust with a new customer when you can hunt down your old customers in their new jobs? Hopefully, your old customers love you—and you can help them build their new careers in their new jobs.

The current market poses a great opportunity to do exactly that. I work with a company called Bluecore that sells exclusively to the retail industry. The retail industry is notorious for employees moving around a lot. One day, their champion, who was the director of merchandising at a big retailer, vanished. Most companies would have panicked and tried to find their new champion. Instead, Bluecore tried to figure out where he went. And it turned out that he had gotten an upgrade and was now the head of merchandising for an even larger retail brand.

He was thrilled when they re-connected with him because it was somebody he knew, loved and trusted from his past. And again, after a series of meetings, they’d landed a deal that was much bigger than their average. The sales cycle for this opportunity was also much shorter because he already knew the value of what he was going to get. In a downturn, I urge you to do more hunting down of your old customers at new jobs. It can really reduce your sales cycle.

Hopefully, your old customers love you—and you can help them build their new careers in their new jobs.


Creativity is your best friend

Weathering a downturn or any sort of economic uncertainty challenges even the most seasoned companies and teams. These growth tips boil down to two core directives: unlock creativity across aspects of the business and deepen your current or future relationships with customers. If you stay true to those two values, your chances to learn more, dig your heels in and grow will multiply.

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