Webinar: Six Lessons Learned Scaling High-Growth Software

By: Matt Buckley  |  March 10, 2023

Recently, Mainsail Partners’ Matthew Buckley hosted a webinar with Kyle Lacy, current CMO at Jellyfish, to offer insight on investing in a company’s go-to-market, brand, customers and teams to scale efficiently and effectively.

Lacy has 17 years of experience in marketing with 12 years in marketing software, primarily at venture-backed companies. His presentation focused on six lessons learned from his tenure at Lessonly. During that time, the company grew from 40 people to 220 people (the Marketing team grew from 10 to 70); and Lessonly was acquired by Seismic.

Lacy’s presentation is available on LinkedIn and the full webinar can be viewed HERE.

Lesson One: A meaningful story scales culture and community. Write a company story that your employees and customers can get behind.

You can spend an inordinate amount of time and resources developing a company’s position, messaging, and story — but if your customers and employees disagree on it, the story will not endure. To effectively write your company’s story, dedicate the time early on to define its origins, missions, visions and values. The writing process should start with the CEO and include Marketing; getting top-down buy-in is essential.

A company’s story scales when employees believe in it and customers sell it, so include both your employees and your customers in the process. Your employee experience should be front-and-center, and your employees need to believe in the story you are telling. Externally, a company’s story can help define you as a thought leader in your space, can help gain competitive edge and can even put you in the middle of a movement.

“The company story is the company strategy.” – Ben Horowitz

Lacy provided an example from his time at Lessonly when the company published a book written by the CEO: Do Better Work. Without discussing the product and with very little self-promotion, Do Better Work captured the story of Lessonly both to its employees and its customers (and prospective customers).

“Do Better Work” became Lessonly’s manifesto. It generated conference topics, inspired a website re-design, impacted employee onboarding, became a branded training method and grew a community. It became a rallying cry for employees and customers alike.

The book helped set Lessonly apart as a thought leader and helped it gain a competitive advantage.

From there, product marketing followed: use cases, personas, one-pagers, etc. but without the story, employees would never have bought in so deeply, which allowed them to in turn strengthen the customer base.

Lesson Two: Make your customers heroes. Great companies are built in partnership with great customers.

Your customers are your best champions, and it is Marketing’s responsibility to manage those relationships. However, Marketing can’t accomplish this alone—Sales, Customer Success and Leadership should also speak with customers weekly to keep their needs central and understand the market.

Track customer success and engagement metrics. Use software like Gong to listen to your prospects and hear their pain points. These tactics make customers feel heard while empowering your teams to drive retention. It’s also critical to create a customer advisory board early on.

Additionally, Marketing should write case studies, feature customers on your website and make them central to your story. Don’t bury your case studies within your site; make them front and center.

At marketing field events, ask your customers to speak to attendees on your behalf, instead of your sales team or executives. Don’t create a presentation about your product; let your prospective leads spend time with your customers (their peers) and your customers will sell your product for you.

“Just put people in a room with your customers and let them talk to one another and share their experiences. They’re your champions!” – Kyle Lacy

Of course, there can be pushback or legal implications from your customers that impact their ability to be featured. To work around these issues, frame this strategy as a celebration of your customer’s success, not as selling your product. To be mindful of how much you ask of your customers, you can request different types of customer feedback, such as quotes, videos, and case studies, and include case study participation and logo use in your contracts.

Lesson Three: Revenue creation supports brand investment. Prioritize driving revenue and pipeline in your marketing budget.

Investors, executives, and partners love to talk about branding — until you miss a pipeline or revenue number. To support your brand investment and earn a seat at the leadership table, Marketing needs to prioritize generating revenue first.

Lacy suggests the following breakdown of Marketing budget as your goal spend:

  • 50-70% to revenue-generating activities
  • 30% focuses on building brand
  • 10-20% for operational efficiency

Before you spend money on brand or operational efficiencies, Marketing spend should be focused on driving revenue. If Marketing successfully drives revenue, you’ll have the budget and momentum to expand or scale your more innovative projects.

Lesson 4: Marketing should be experiential and (a little) irrational to drive creativity. Be thoughtful about big ideas and take big swings. New ideas differentiate brands and build memorable experiences.

When you allow creative teams to think outside a lead or revenue number, they often end up brainstorming innovative and successful strategies—which is why it’s important to strike a balance between targeting company metrics and supporting creativity.

One example Lacy gave was using direct mail as a differentiator. At Lessonly, as part of the Do Work Better campaign, the company shipped over 5,000 golden llama statues (their mascot) to customers, individuals, and prospects who embraced their company mission. The result? The first 2,500 llamas sourced $3M in pipeline and $150K in closed-won deals—all without focusing on any product marketing.

Another way to market successfully is to invest in your customers. During the COVID-19 pandemic, Lessonly noticed many of their customers suffering from layoffs, so Lessonly “irrationally” cut all spending and reinvested in two campaigns:

  1. Hired career coaches for customers and hosted virtual events to help ex-customers find new jobs.
  2. Designed coloring books and board games for parents stuck at home with kids.

This led to customer happiness and satisfaction, as well as retention, and it turned their customers into champions.

Lesson Five: Encourage alignment through shared goals. Marketing should own a revenue or pipeline number to earn a seat at the table and force alignment between revenue-generating teams.

“Sales and marketing must be aligned. That’s it,” says Lacy. Marketing should own a pipeline or revenue number because that builds sales alignment and shared goals and gives Marketing a seat at the table.

When you’re responsible for reps’ quota attainment, you’ll hear from that team. It’s important for Marketing to understand why Sales spends so much time on attainment. If your Sales and Marketing teams aren’t aligned, you need to have a conversation to re-align goals to become efficient and effective.

One way to align Sales and Marketing is to draft a revenue handbook for service-level agreements between revenue-bearing teams that delineates territories, provides funnel definition, and sets account ownership rules and rules of engagement. You can adjust these goals on a biannual basis.

Marketing should support the entire Sales funnel, not just the top. Implement customer marketing and headcount capacity modeling to increase net-dollar retention (NDR) and to understand how many AEs need to be hired to hit the pipeline-to-revenue goals for the year. As marketers, it’s critical to understand this balance so you can understand budget trade-offs to avoid falling behind on headcount capacity.

Lesson Six: Invest in your team’s career and jobs. Individuals with great managers do not need a resume to get their next job.

To invest in a team-first mentality, Lacy suggests using personality tests like DiSC to help better understand the way everyone works; reading 5 Dysfunctions of a Team and discussing ways to build trust, vulnerability and teamwork; and hosting a “Life Story” meeting during which each direct report creates a story slide detailing their personal and professional triumphs and challenges.

To think beyond qualitative and tactical goals, track personal development plans. Discuss career aspirations with your employees and use career goals to promote networking, career development, reading, etc.

This will pay huge professional dividends over the course of both your careers.

Additional lessons learned

  1. Hire product marketing and a great designer early.
  2. Budget size doesn’t matter; scale and move quickly.
  3. Go-To-Market channel strategy eventually hits a ceiling.
  4. $30MM is about testing and iterating -> $300MM is about process and maintenance.
  5. Marketing is only successful if revenue goals are met.
  6. Organic search is necessary to any demand gen and content strategy.

Matt is a Vice President at Mainsail Partners. He works with Mainsail’s portfolio companies to implement marketing and sales strategies to fuel growth.
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