September 14, 2022

Lessons from Leslie Fine: Board meetings, scaling sales teams, storytelling

pexels fauxels

Networking with industry leaders is key to evolving your business. These connections help you information swap on current big issues, including shifting dynamics in the tech industry and what’s on the horizon.

The annual invite-only Scaletech Conference provides a unique opportunity to network while tackling these big questions. Through four expert speakers covering topics like data science, cloud computing, virtual platforms and artificial intelligence, the event is a chance for companies to get answers to their most pressing questions. Since the event’s inception, Scaletech has grown to focus on building technology at scale and successfully delivering these products.

Here are some key takeaways from the first session with Leslie Fine, General Partner at Enjoy the Work.

Use your board as a resource

Remember that your board is there to help you and that you can, and should, use them as a resource. In many ways, you as CEO are the customer but the quality of the outcome depends on what you put into it. Clarity of agenda, coming with a point of view rather than a report and being crisp on actions and follow throughs are the building blocks to making that quarterly meeting productive.

Don’t omit the real issues facing your organization from board meetings – aka the challenges keeping you up at night. Your board is investing their time and their money to help you be successful realizing the company’s vision. Leverage them to help you find solutions to your big hairy issues.

Have clear agreements with your board on what is the ultimate goal that you’re working backwards from (an exit, a raise, or profitability) and what you collectively believe has to be true to achieve it in the time you have. From there, you can work backwards and align on goals. Use your board to gain alignment on your plan: what are potential blind spots? Are your targets achievable? How could they be altered or improved?

De-risk investment for investors

Your first job in building a relationship with an investor is to help them see a clear and painful problem in the world that will inevitably be solved. From there, your goal is to highlight why your product and leadership team are the best possible investments on the path to that solution.

Once an investor sees the world the way you do, it’s all about mitigating risk. If there’s anything unusual about your fundraise, having empathy for your investors’ goals and concerns can help you see the path forward. For example, if you have a cap table structure that creates challenges for them, learn what targets they have. Is there an ownership target for them? For the founders? What does their ideal structure look like, and where do you have flexibility?

Other considerations? Consider how voting rights are evaluated and whether to prioritize common shares over majority shares, which could help alleviate uncertainties surrounding control and ownership that some investors may have.

Finally, new investors will feel more confident if the founders and those running the company are bought in enough to lead the company to success.

Culture is important when shifting from Series A to B

As you transition from Series A to Series B, product-market fit is proven and you will experience massive acceleration. What will hold the ship together as it accelerates is your culture and your values. Although “value-setting” and “culture” can sometimes be seen as high-level, abstract ideas. In reality, they’re key pieces of running your business.

Your values define who you are, your culture, and the philosophy with which you bring your products into the world. Core values are the language of a company. Language allows people to move faster. It allows them to solve problems, resolve conflicts, and celebrate successes more seamlessly. 

Ideally, your values have been defined and codified early in your company’s history. If not, now is the time. As you grow, as you see people in the halls that you never interviewed yourself, your values will hold the culture together.

Understand how deep the trust is in your leadership team – if your leaders don’t have total trust in each other, and an effective way to communicate and find solutions, then you’re going to run into challenges and breakdowns as you scale. Read 5 Dysfunctions Of A Team by Patrick Lencioni for more on trust in leadership.

Bottom line: take the time to build a high-functioning leadership team. If you can define your values and instill them into the way that your leadership team functions, the culture of your organization will flourish and align with your long-term goals.

Tell a compelling story

According to Joseph Campbell’s concept of the hero’s journey – based on his work, The Hero with a Thousand Faces – there is a universal storytelling device, which has worked for thousands of years across many human civilizations. In a nutshell, it begins with a world that becomes out of balance and needs a hero who goes on a journey, finds a helper, and ultimately is transformed, and comes back triumphant.

This narrative framework can also be applied to your organization. Consider how the world is out of balance. The hero who arrives to put things back into balance is the person experiencing the pain – your customer. You and your team, in this context are the “helpers” – how can you help the hero be transformed? 

How do investors fit in? They’re often unaware that a problem exists. To tell then your story in a compelling way, you want to create sticky stories that they won’t forget. Remember that your customers are the heroes in your story – you want to put them at the center of your story and encourage them to see how you will help them get to be transformed—a.k.a. a stronger, better business.

Set realistic goals

When it comes to working at a startup, people are generally looking for three things: autonomy, mastery, and purpose.

These are important considerations when it comes to goal setting for your business; how are your goals addressing each of these three objectives? By aligning the everyday activities of the team to the company’s goals we can create a steel thread that allows people to find purpose, have autonomy over how they work, and become masters. Avoid creating siloes among teams, where one team’s goals are disconnected from the organizational goals.

One way to get there is by centering leadership meetings around the organization’s goals – making them the “agenda” of your business. How is the company measuring up? Are goals being integrated throughout each quarter?

Incentivizing your sales team

When structuring your sales team’s compensation, remember that a startup is a temporary organization in search of a business model — and that this search requires hypothesis testing and shifting goals. 

Your sales team will still have targets. Where startups get into trouble is when those targets are not aligned to what the business needs to demonstrate next or are not adjusted at a cadence that keeps everyone aligned. A team that is incented to sell anything to anyone, rather than comped only for specific use cases with specific success metrics, can create noise and waste. 

Don’t be afraid to change these fairly frequently. One strategy is setting up quarterly compensation plans, instead of annual. With this approach, your sales teams understand that these lines may shift quarterly, and although these shifts may be rare, it gives the flexibility for adjustments if predictions or the math needs to be changed.

Interested in learning more? Check out the Scaletech Conference or apply to join CoLab, Georgian’s collaborative pre-investment program for early-stage startups.

Growth insights
in your inbox

Join our community of thousands of tech entrepreneurs to get actionable insights from our monthly newsletter.