Chapter 8

Sales Career Development

Helping reps grow with a Japanese philosophy called Ikigai.

In February, 2017, Stan Massueras joined Intercom as its new Director of EMEA Sales. From the outside, it might have looked like a cushy job: the California-based communication technology company had just wrapped up its fourth multimillion dollar funding round and was doing more than $50M in Annual Recurring Revenue—and it had achieved all of that in just three short years.

But Massueras quickly spotted a structural challenge: Intercom’s career development felt like a “box-ticking exercise.” Employee reviews, where each employee’s personal and professional performance was evaluated, were surface level and rarely touched on anything substantive. And as the startup ballooned in size, reps were quickly bumped up the corporate ladder. These promotion decisions, as in most early-stage startups, were based on revenue targets—and that was a problem.

The misguided career-development system created a retention issue, although it wasn’t people leaving too quickly that concerned Massueras. Intercom was growing—fast—and people were getting comfy in their seats. “It was a special environment,” he explains. “Our attrition rate was low because people thought Intercom was taking off.” Instead of looking for their next challenge, employees were hunkering down, waiting to see how large the company got.

While four- and five-year tenures might have felt like a victory, Massueras says he wasn’t convinced. “If you can't keep people super-motivated and continue to challenge them, that's when you breed toxic mentality on the floor,” he says.

And when people stay in the same role indefinitely, that’s exactly what happens.

Instead of building retention around time, Massueras suggests sales managers flip their mindset and focus instead on productivity. The goal is to maximize the productivity and motivation of a rep while they’re with your company. “How can you get them ramped and onboarded and really excited to work with you in the fastest amount of time?” he says. “How can you help them crush their numbers, while developing long lasting skills?”

At Intercom, Massueras put this radical theory to the test, overhauling the sales org’s career development process and preparing the company for its next phase of growth.

Get to Know Each Other

Before Massueras joined Intercom, he worked at Facebook, building its sales org for France and Benelux. While the then-five-year-old, California-based social network was already enjoying significant growth in terms of users, it wasn’t yet the all-powerful tech giant we know today. Like Intercom, Facebook’s career development was an afterthought.

In Facebook’s high-growth environment there just wasn’t enough time for in-depth career development, the process of identifying professional goals and working towards them. What few career-development conversations Massueras had with his managers were treated as a HR formality and the focus was placed firmly on his commercial performance. “In sales, you're often only as good as your last quarter,” Massueras says. “So it's very hard to have an effective retrospective on how you've performed over the past 12 months.”

At Intercom, Massueras challenged himself to design the career development framework that he would have wanted as an individual contributor. After much research, he pitched a new career development framework to his frontline managers. “I presented it to my management team,” Massueras says. “Then we refined it and actually decided to launch it a couple of weeks after.”

Massueras' new career development framework, which he dubbed Individual Development Plans (IDP) started with a simple premise: he wanted to get to know his direct reports better. By understanding his direct reports as more than just sales figures, Massueras says he learned how to make each person’s role more rewarding.

A quote from Stan Massueras reading "If you can motivate people in their personal lives and they can absorb that into their professional life, that’s how you turn their job into a vocation."

He knew that people with a passion worked harder and faster. But more importantly, he could keep his reps motivated, challenged, and performing at their best.

To push past basic sales statistics and learn about his direct reports as people, Massueras invited each of his reports to an introductory meeting, which he split into three separate conversations.

During the first conversation, Massueras tries to find out about the jobs people are passionate about. To do so, he asks a simple question: “If you were given $10 million dollars so you don't have to worry about money for the rest of your life, what job would you like to do?”

Throughout this conversation and the two that come after, Massueras is careful to allow his direct reports to lead the conversation—and doesn’t constrain their thinking to just roles at Intercom.

If someone identifies a future career path within Intercom, that’s great, he says. But sending the message to employees that you expect them to commit to your company long-term can be dangerous. “One big mistake that larger tech firms make is to try and retain for way too long,” Massueras says. “As a result, employees turn into toxic and only a minority of them will continue to remain motivated and deliver positive results.”

Massueras recalls a conversation that one of his managers had with a top account executives at Intercom, who told him that her dream was to be a television personality. Using the IDP framework, Stan’s manager immediately took that dream job and worked out how he could tweak his direct report’s current role to help her get there. “She's now the face of all our LinkedIn videos,” he says. “She's doing an amazing job and can develop new skills while making her role richer.”

To people on the outside, it may look like Massueras is pushing his best employees out of the company but what he’s really doing is maximizing their performance while he has them.

In their second conversation, Massueras prompts his direct reports to think about what jobs they would be good at with the skills, interests, and knowledge they already have.

Again, Massueras recalls his top-performing AE. As an aspiring television personality, she had outstanding public speaking and presenting skills, which made her a great fit for conference speaking gigs. “It wasn’t really part of her job,” Massueras says. “But now when I can't attend a conference, she will do it—and I know that she will do a great job, because we had this conversation.”

During the third and final conversation, Massueras asks his direct reports to choose a role where they can learn new skills. “It shouldn’t be carpentry or origami,” Massueras says. “The skill has to be related to a specific career.”

Since Massueras’ top-performing AE wants to work in media, it’s likely that she wants to understand the technical elements of production. In that case, she would learn lots of useful new skills in a media research or production role.

At the end of his three conversations, Massueras is left with a big pile of career paths. His next job is to help his direct reports sift through this pile of possible options and select a handful of appealing careers.

Illustration of the collaborative learning at Intercom

Analyze Your Current Situation

Massueras knew those initial conversations would produce a number of disparate ideas that would be tough to whittle down. For that, Massueras incorporated a Japanese philosophy called Ikigai, which translates to "a reason for being.”

Massueras’s subtley adapted Ikigai is best illustrated as a Venn diagram with four overlapping circles—what we love, what we’re good at, what we can be paid for, and where I can learn and develop new skills. The area covered by each intersecting circle represents Ikigai. “Japanese people spend so much time at work,” Massueras says, “so if they can find happiness and meaning at work, they will live a happy life.”

Overlaying the Ikigai diagram on their earlier conversation allowed Massueras and his direct reports to filter out idealistic or ill-fitting roles, and select careers that were good for healthy, long-term aspirations.

To demonstrate how the concept works in practice, Massueras often shares his own career progression with his direct reports.

At Facebook, Massueras had spent years surrounded by people who were ripping up the rule book and reinventing the social media landscape. It was inspiring to watch and eventually Massueras decided to find his own niche to revolutionize. “I opened my own company, Pulp,” he says, “and over two years we tried to build a competitor to Instagram.”

The idea was interseting—Pulp was more or less the precursor of TikTok—but it didn’t go well in practice. “I was a terrible entrepreneur,” Massueras admits. “I loved the mission part and I was learning a lot but I wasn’t making any money and I wasn’t good at it.”

With just two of the four concepts ticked off, Massueras admitted he fell a long way short of true Ikigai.

Once Massueras’ direct reports understand how Ikigai works, he takes their career options and, one by one, tests them against the Ikigai concepts.

If someone wants to be a Partner at a VC firm but lacks natural financial acumen, Massueras shows them that they’re missing the ‘what you’re good at’ segment and gently dissuades them from the idea. Likewise, if someone wanted to do something wildly unprofitable —say, start a new electric automaker with just $500 seed capital—Massueras might challenge them to explain how they’ll ever turn a profit.

Using the lens of Ikigai, Massueras helps his direct reports identify three roles that are achievable in the next three to five years and personally rewarding according to Ikigai. “You might want to be a TV personality or a marketing director or to work for Amazon in marketing,” Massueras says, imagining a conversation.

Once Massueras has three roles set, he does… nothing.

He knows Intercom’s IDP framework is unusual and he doesn’t want to pressure his direct reports into a knee-jerk decision. So after landing on three potential roles, Massueras and his direct reports pause their conversation for two or three weeks.

Create a Roadmap

After their break, Massueras arranges a second meeting, during which he asks his direct report to settle on one option. “Let’s say you want to be a sales operations manager,” Massueras says. Now Massueras understands their desired destination, he can help his direct reports work out a way to get there. And that all starts with finding a role model.

For instance, Intercom recently hired a new Sales Operations Manager named Steven Perini. He came to the company with a great pedigree and considerable experience. For a budding sales operations professional, he makes a great role model.

Massueras takes the role model—in this case, Perini—and challenges his direct report to explain what four skills help them excel in their role.

Perini is the sales operations manager for North America and Asia-Pacific. It’s his job to build and manage our Operational infrastructure and Reporting to help sales reps sell better, faster, and more efficiently.

First, sales operations managers need to work with dozens of different departments—sales, marketing, operations, product, management—so excellent communication skills are paramount. Second, Perini also needs an in-depth understanding of the sales process as without it he’s just shooting in the dark. So comprehensive knowledge of sales is also important. Third, understanding how his work contributes to Intercom’s larger business goals is essential for accurate and effective reporting. In other words, Perini needs to possess a strong business acumen. And fourth, he needs technical competence—he must understand what he’s selling.

Once Massueras has identified all four key skills, he grades both Perini and his direct report on each. Since Perini excels in his role, Massueras gives him ten out of ten for each. But Perini’s direct report, who is just starting out, will likely score much lower. “For communication, I’ll give you a five,” Massueras says, imagining a conversation. “For sales knowledge, six. For business acumen, three. And so on.”

The grades create a baseline, from which Massueras will help his direct reports improve. To do that, he identifies three or four activities the rep can perform to improve their performance in a particular skill. For Perini’s protege, Massueras suggests they present at conferences to improve their communication skills and review a dozen key territories to develop their general business acumen. Massueras also tasks the rep with designing three or four activities of their own. This helps them learn how to analyze their own skills and design their own improvement plan.

After handing over the list of activities and initiatives, the onus moves onto the direct report. It’s up to them to own their development. “My job is to facilitate career development,” he says. “But I'm not going to bring them a promotion on a silver tray. It's up to them to take on this journey.”

Illustration of the individual development plan at Intercom

Tracking Progress

With the roadmap designed, Massueras steps back almost entirely. He doesn’t prod or poke or guide—it’s entirely down to the individual sales rep to manage their own development. Massueras’s only interaction is to track their progress. “We will track how they’re progressing and hold them responsible,” he says.

At the end of the six-month period, Massueras meets again with his sales reps and reviews their progress. “We have a timeline measuring whether each rep is on track,” he says. But even if a rep has checked off all their activities and dramatically improved their skills, they aren’t guaranteed a promotion.

“[The IDP] is designed to give you a competitive edge if your dream job opens up,” he adds. “If there is an opportunity for you to move into, for example, management, [the IDP] helps you kick ass during your job interview.”

Over three years, Massueras has seen dozens of employees work through their IDP and move towards their ideal job—sometimes helping them move upwards within Intercom and other times helping them move out to a different company.

At the end of 2019, for example, he said goodbye to one of Intercom’s top-performing account managers. During the employee’s final IDP, Massueras helped him choose between a new role at Intercom and a new role somewhere else. After more than four years at Intercom,the account manager felt the challenge at Intercom had disappeared so he opted to move to a Fintech startup, where he’s now building the European sales org.

“I'm sad to see him leave the company but I sincerely know that it is the best thing for him and it’s also the right message to share with the 40 people behind him,” says Massueras. It’s a loss but having him succeed is a huge motivator for the people on the sales floor.”

Building Rewarding Roles

After implementing Intercom’s new career development process, Massueras lost some of his top employees. They had been promoted during Intercom’s rapid expansion and were now languishing in ill-fitting senior roles. “It was a pretty unpopular decision to make, but it had to be done,” Massueras explains. “It’s paying off now because now we've got the right mentality and philosophy in our team.”

Through Massueras’s new IDP, he empowered his direct reports to take back control of their careers. And that transfer of control is important. By focusing on where the individual report wants to go in three to five years, Massueras makes sure their current role is as fulfilling and rewarding as possible. And that produced employees who are more engaged, innovative, and loyal.

Now, Intercom’s senior sales org is packed with people who want to be there, albeit not necessarily indefinitely. “We use an IDP to maximize the productivity and the motivation of our reps,” he says. Even if they won’t stay forever, while employees are working at Intercom, Massueras knows they will give their absolute all and help the company grow into the technology giant everyone knows it can become.