Skip to content

Series B & C: How do you scale a business that does good?

, |By Jason White

People and culture matter at every stage of an organization’s lifecycle — but they play a particularly critical role in establishing the foundation of a scalable business in the beginning stages, with very clear implications for pay equity, pay transparency, and compensation.

On the most recent episode of High Growth Matters, we spoke with James Cleveland, Head of People and Culture at Landed. James specializes in scaling fast-growth organizations with social impact missions during the crucial time when product-market fit has been achieved and go-to-market fit needs to be figured out post haste. He's done so as a founder, COO, Chief Talent Officer, Chief People Officer, and more for several decades.

This blog has been adapted from that conversation and covers:

  • The importance of a 3 to 4-year plan and how to bring one to life
  • Guiding principles for building leadership trust - including pay equity and pay transparency
  • Assembling a people team that is foundational for scaling

Subscribe to the show on your favorite podcast player, such as Apple Podcasts or Spotify. Don’t miss the full episode: Series B & C: How do you scale a business that does good?

Sign up for free.


The importance of a 3-4 year plan and how to bring one to life

After decades of working with mission-driven startups, James has discovered a few tips and tools that are instrumental for scaling. One thing he has found to be invaluable across the board is a 3 to 4-year plan. 

“Most individuals who come to early-stage organizations really need some level of certainty of where they're going,” James says. “Employees want to know how they’re connected to the bigger plan.”

While long-term goals can be challenging to define, particularly in the early stages, creating a vivid description for employees to share is crucial. Without one, employees will often have their own ideas of success and aim their efforts in different directions, creating disorder and slowing growth.

How to create a vivid description

“I get teams to participate in exercises of defining success,” James says. “They decide what it looks and feels like and help decide how we can get there.”

Once you’ve established a precise definition, you can prioritize resources and effectively and efficiently work through a plan. People gain agency and understanding of how they can contribute to the bigger picture.

Bringing your plan to life with a talent strategy

With a long-term plan, it is much easier to make critical decisions about the people within a company, the potential acquisition of new skills and efforts for internal training. 

Rather than bringing in skills to solve existing problems, organizations with a 3 to 4-year plan can proactively upskill employees or recruit talent from outside sources to help the business through each stage of scaling. 


5 guiding principles for building leadership trust

Having the right people in the right positions can spark immense growth — particularly when leadership is enabled to recognize and nurture top talent. But great leaders aren’t born. People become effective leaders by embarking on a journey that requires intentional investment and personal growth.

James shared a few guiding principles leaders can adopt to build trust:

1. Actively communicate in small, meaningful ways

James has found that truly effective leaders make an effort to connect with people beyond their immediate team — and these efforts don’t need to be grand or expensive.

“Every now and then, have lunch, host a conversation, say hello to everyone, not just their leaders,” James says. “Get to know how people are doing, and share things about yourself.”

2. Actively engage with direct reports

According to James, the best leaders are engaged with their direct reports beyond their professional growth.

Effective leaders also ask direct reports about their own team members. Taking up a regular curiosity, they seek to know who up-and-coming leaders and high performers are. 

3. Provide stretch opportunities

The best leaders also provide their people with stretch opportunities. Eager to explore innovative ideas and test new strategies, these leaders will bring promising and interested people to contribute.

Providing stretch opportunities opens a two-way avenue for trust and allows leadership to identify new talents in existing employees while also fostering connection. 

4. Be actively involved in recruiting 

“The leaders who care about people and culture spend between 30 and 50% of their time in recruiting mode,” James says. 

Whether these leaders are on LinkedIn, having conversations with people, connecting at events, or participating in interviewing and hiring processes, effective leadership will be invested in who is coming into the organization. 

5. Participate in cultural norms

Great leaders are not above workplace cultural norms and rituals — they actively participate in them.

To be an effective leader, you must be invested in perpetuating culture throughout your team, organization and daily life. There are big implications here for pay equity and pay transparency,


Assembling a people team that’s built to scale

As an effective leader, it’s important to train employees in a manner that factors in their professional goals while also lending to business needs. While it can be difficult, there are a few things you can do as a leader to maintain this balance, according to James. 

1. Identify core competencies

Every company has a unique set of requirements and capabilities necessary for delivering its product or service while maintaining true to its unique culture.

Before you can foster optimal core competencies and behaviors, you have to identify which are most successful within your organization. 

2. Add new frameworks

“Managers — especially those who are new to leadership — often have a lot of pressure to deliver results,” James says. “They tend to default to what they know and how they have been managed.”

Challenging managers with new frameworks breaks the cycle of ineffective leadership. It also forces leaders into positions where they recognize that the people they are working with have a wide range of skills, communication styles and needs. Determining these differences allows managers to approach leadership styles in a way that maximizes each person's potential.

3. Encourage critical thinking

“Effective leaders need to think critically about who they are as a manager and how they need to connect with their people,” James says. “I have yet to see a successful one-size-fits-all approach.”

4. Utilize personality tests 

Recognizing that everyone is different and cultivating empathy for those differences is paramount for effective leadership. Personality tests are one way to provide tangible ways to define those differences.

Further, these tests help solidify the two-way relationship between management and direct reports that’s necessary for successful professional growth.

“It opens a dialogue and puts part of the burden on the employee,” says James. “Employees cannot wait for a manager to provide what they need. They have to advocate for themselves to be successful as well.”

To hear this episode, and many more like it, you can subscribe to The High Growth Matters Podcast on our website, Apple Podcasts, Spotify, or just search for The High Growth Matters Podcast in your favorite podcast player.