Five Leadership Insights From An 8-Figure SaaS CEO

Alison Taylor, Co-Founder & Co-CEO, Jane

SAAS NORTH NOW #39

Hello to Canada’s SaaS Community,

For years, Alison (Ali) Taylor built Jane App quietly. She didn’t aim to make splashy media headlines or fundraise a huge amount from blue-chip venture capitalists. Instead, she focused on making revenue—and she made plenty of it. Now past the 8-figure mark, Ali spoke with SAAS NORTH to share insights for scaling founder-CEOs.

Key takeaways:

  • Budgeting should be done collaboratively between executives so everyone sees where the money is going.
  • Whenever possible, give employees a voice in decision-making and give them a choice in which path of action they take.
  • Data tells you where to look but it doesn’t give you the answer.

Dave Tyldesley

Co-Founder/Producer, SAAS NORTH Conference Editor, SAAS NORTH NOW

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As your startup grows, your job as a founder changes as well—you must continue to evolve to be the leader your business needs. Alison (Ali) Taylor knows this evolution well, having built and scaled Jane App from nothing to over 8-figures in annual revenue.

Speaking with SAAS NORTH, Ali shared five leadership insights from her journey so far.

1. CEOs need to evolve from soloists to conductors

When Ali started Jane App, she spent upwards of 90% of her time speaking with customers. As the company grew, that changed. At first, she worked double duty as a “player-coach,” both talking to customers directly and managing employees. But then things evolved further and she took an additional step back.

“As the company scales—we’re at 375 people—you’re working with leaders of departments that are working with the managers that are working with that team,” said Ali. “And so you go from being like a soloist, to the head violinist of a group, and then you become just eventually this conductor.”

This evolution from soloist to conductor means that instead of focusing on individual customer needs, Ali thinks about the bigger picture of customer trends and how that impacts future decision-making. She also focuses on bringing in competent leaders, with the company hiring a Chief People Officer and a Chief Marketing Officer in the past year.

2. Spend the company’s money together

Ali said a key element that allowed Jane App to scale—the thing she has to “defend and maintain” as the company continues to grow—is collaborative budgeting.

Jane App has been revenue positive since its early days and has taken very little outside funding compared to revenue. Further, Ali refuses to hire without existing revenue to pay that new person’s salary.

With these budgetary constraints in mind, Ali said it’s critical to work together on budgets. This often requires “reprogramming” the mindsets of new executives, particularly those who come from VC-backed companies and aren’t used to this kind of budgeting approach.

“It’s a very thoughtful budgeting process that’s very collaborative with all of our execs because we’re all spending Jane’s money together,” said Ali.


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3. Customer experience and employee experience are connected

Ali said a secret to Jane App’s scale is how well customers are treated. But instead of freebies or flashy customer marketing campaigns, Ali focused on treating employees exactly how she wants them to treat customers: with care and respect.

At Jane App, that looks like a few different programs:

Voice and choice: Whenever possible, employees are given an opportunity to voice their opinions on something that will impact them (e.g. roadmap decisions, new processes, etc.). From there, again whenever possible, employees should be given a choice about which path to take.

In some cases, giving employees a choice isn’t feasible. For example, Jane App recently added long-term disability insurance coverage for employees, which requires paycheque deductions due to tax rules. In cases like these, Ali said it’s critical to communicate what’s changing, why it’s changing, and the impacts it will have. However, these types of unilateral decisions should be limited.

Manager support: Ali said she likes to flip the traditional hierarchy—instead of a top-down command system, it’s a bottom-up support system where higher-ups focus on helping individual contributors be more successful. At Jane App, that looks like a manager who is dedicated to supporting eight individual contributors.

Sharing with customers: Whenever Jane App’s team comes up with a solid internal process, they think about whether their customers might benefit from it as well. For example, the team conducts regular team meetings on the company’s mission, vision, and values, so they shared that template with their customer base.

“If I want our support team to treat our customers with respect and to show up in a way that’s like kind and supportive and positive, then they need to be working in an environment that has all those things,” said Ali.

4. Data is not the answer

Ali said she loves data but gets concerned when she sees other entrepreneurs treat it like the holy grail.

“As soon as you put something in a chart, everyone thinks it’s a fact or truth,” said Ali. “That’s not how data works.”

The problem with data, said Ali, is that it’s fallible. To illustrate this, she shared the example of the Hanoi rat massacre of 1902. The city wanted an efficient plan to exterminate rats from the sewer system and thus offered a bounty for citizens to kill rats—specifically, a payment for every rat tail. But it failed spectacularly. Many citizens simply cut off rats’ tails rather than actually killing the rat. Others went even further and started breeding rats so they could make more money.

“If you look at the numbers in isolation, you don’t always know what you’re looking at,” said Ali. “Like someone who doesn’t answer as many phone calls as someone else. Maybe they’re not working hard or maybe they’re just creating really amazing customer experiences. So until you dig deep, you won’t know. Data only tells you where to look. It is not your answer.”

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5. Harness the hamster wheel

Focusing on employee experience doesn’t mean Jane App employees don’t work hard—quite the opposite. Because Ali and the team only hire when there’s revenue to pay the person’s salary, it means there’s always a shortfall of resources compared to work: the existing team brings on a customer, which creates a support gap. That customer’s revenue is used to fill that gap.

“Our culture for the team has always been one of just sprinting because we’re always behind on hiring,” said Ali. “It’s always been a hamster wheel.”

At the same time, Ali is conscious of not running the business in a “burn fast, burn bright, burn out” kind of way. Instead, she prioritizes sustainability, making decisions that benefit the long-term rather than simply closing the next dollar.

“We want to have long, sustainable, healthy business, with long, sustainable, healthy employment,” said Ali. “We have people that have been with Jane for eight, nine, or 10 years—people stick around.”


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Hello to Canada’s SaaS Community,

For years, Alison (Ali) Taylor built Jane App quietly. She didn’t aim to make splashy media headlines or fundraise a huge amount from blue-chip venture capitalists. Instead, she focused on making revenue—and she made plenty of it. Now past the 8-figure mark, Ali spoke with SAAS NORTH to share insights for scaling founder-CEOs.

Key takeaways:

  • Budgeting should be done collaboratively between executives so everyone sees where the money is going.
  • Whenever possible, give employees a voice in decision-making and give them a choice in which path of action they take.
  • Data tells you where to look but it doesn’t give you the answer.

As your startup grows, your job as a founder changes as well—you must continue to evolve to be the leader your business needs. Alison (Ali) Taylor knows this evolution well, having built and scaled Jane App from nothing to over 8-figures in annual revenue.

Speaking with SAAS NORTH, Ali shared five leadership insights from her journey so far.

1. CEOs need to evolve from soloists to conductors

When Ali started Jane App, she spent upwards of 90% of her time speaking with customers. As the company grew, that changed. At first, she worked double duty as a “player-coach,” both talking to customers directly and managing employees. But then things evolved further and she took an additional step back.

“As the company scales—we're at 375 people—you're working with leaders of departments that are working with the managers that are working with that team,” said Ali. “And so you go from being like a soloist, to the head violinist of a group, and then you become just eventually this conductor.”

This evolution from soloist to conductor means that instead of focusing on individual customer needs, Ali thinks about the bigger picture of customer trends and how that impacts future decision-making. She also focuses on bringing in competent leaders, with the company hiring a Chief People Officer and a Chief Marketing Officer in the past year.

2. Spend the company’s money together

Ali said a key element that allowed Jane App to scale—the thing she has to “defend and maintain” as the company continues to grow—is collaborative budgeting.

Jane App has been revenue positive since its early days and has taken very little outside funding compared to revenue. Further, Ali refuses to hire without existing revenue to pay that new person’s salary.

With these budgetary constraints in mind, Ali said it’s critical to work together on budgets. This often requires “reprogramming” the mindsets of new executives, particularly those who come from VC-backed companies and aren’t used to this kind of budgeting approach.

“It's a very thoughtful budgeting process that's very collaborative with all of our execs because we're all spending Jane's money together,” said Ali.


3. Customer experience and employee experience are connected

Ali said a secret to Jane App’s scale is how well customers are treated. But instead of freebies or flashy customer marketing campaigns, Ali focused on treating employees exactly how she wants them to treat customers: with care and respect.

At Jane App, that looks like a few different programs:

Voice and choice: Whenever possible, employees are given an opportunity to voice their opinions on something that will impact them (e.g. roadmap decisions, new processes, etc.). From there, again whenever possible, employees should be given a choice about which path to take.

In some cases, giving employees a choice isn’t feasible. For example, Jane App recently added long-term disability insurance coverage for employees, which requires paycheque deductions due to tax rules. In cases like these, Ali said it’s critical to communicate what’s changing, why it’s changing, and the impacts it will have. However, these types of unilateral decisions should be limited.

Manager support: Ali said she likes to flip the traditional hierarchy—instead of a top-down command system, it’s a bottom-up support system where higher-ups focus on helping individual contributors be more successful. At Jane App, that looks like a manager who is dedicated to supporting eight individual contributors.

Sharing with customers: Whenever Jane App’s team comes up with a solid internal process, they think about whether their customers might benefit from it as well. For example, the team conducts regular team meetings on the company’s mission, vision, and values, so they shared that template with their customer base.

“If I want our support team to treat our customers with respect and to show up in a way that's like kind and supportive and positive, then they need to be working in an environment that has all those things,” said Ali.

4. Data is not the answer

Ali said she loves data but gets concerned when she sees other entrepreneurs treat it like the holy grail.

“As soon as you put something in a chart, everyone thinks it's a fact or truth,” said Ali. “That’s not how data works.”

The problem with data, said Ali, is that it’s fallible. To illustrate this, she shared the example of the Hanoi rat massacre of 1902. The city wanted an efficient plan to exterminate rats from the sewer system and thus offered a bounty for citizens to kill rats—specifically, a payment for every rat tail. But it failed spectacularly. Many citizens simply cut off rats’ tails rather than actually killing the rat. Others went even further and started breeding rats so they could make more money.

“If you look at the numbers in isolation, you don't always know what you're looking at,” said Ali. “Like someone who doesn't answer as many phone calls as someone else. Maybe they're not working hard or maybe they're just creating really amazing customer experiences. So until you dig deep, you won't know. Data only tells you where to look. It is not your answer.”

5. Harness the hamster wheel

Focusing on employee experience doesn’t mean Jane App employees don’t work hard—quite the opposite. Because Ali and the team only hire when there’s revenue to pay the person’s salary, it means there’s always a shortfall of resources compared to work: the existing team brings on a customer, which creates a support gap. That customer’s revenue is used to fill that gap.

“Our culture for the team has always been one of just sprinting because we're always behind on hiring,” said Ali. “It’s always been a hamster wheel.”

At the same time, Ali is conscious of not running the business in a “burn fast, burn bright, burn out” kind of way. Instead, she prioritizes sustainability, making decisions that benefit the long-term rather than simply closing the next dollar.

“We want to have long, sustainable, healthy business, with long, sustainable, healthy employment,” said Ali. “We have people that have been with Jane for eight, nine, or 10 years—people stick around.”