The Unlikely Path To A Joyful Sales Career

️ ️⚡ Today’s level up ⚡

Today’s edition dives deep into the importance of bringing joy into our challenging role as a modern revenue generator, which comes from a place that may surprise you.

Let’s go!

A quick lesson from Jewel

I thoroughly enjoyed reading Slow Productivity by Cal Newport.

Without spoiling all of its goodness (I highly recommend reading the book), Newport defines Slow Productivity as:

A philosophy for organizing knowledge work efforts in a sustainable and meaningful manner, based on the following three principles:

1. Do fewer things.

2. Work at a natural pace.

3. Obsess over quality.

He argues that Slow Productivity is a stronger alternative to producing better work and reducing burnout compared to how productivity is measured today in most environments of the knowledge economy. He calls this Pseudo-Productivity:

The use of visible activity as the primary means of approximating actual productive effort.

Throughout the book, Newport contrasts the modern emphasis on visible productivity (like emails and meetings) with historical examples where significant achievements (like those of Isaac Newton, Jane Austin, and others) were made over longer periods of time with a focus on deep work and high quality standards.

In the third principle, Obsesses Over Quality, he references one of my favorite examples in the book, which highlights the rise of the singer Jewel.

In the early 90s, Jewel was living out of her car in San Diego and performed every Thursday night at the Inner Change Coffeehouse. What started as a few surfers stopping by to listen to her grew to an audience that packed the coffeehouse and flowed over into the sidewalk outside the venue over several months. Eventually, word got out and it attracted record label executives from Los Angeles.

The story leading up to that point was quite significant, and you can read it in chapter five of the book or listen to Cal Newport tell it in his own words on his podcast Deep Questions.

But here’s where the story gets really interesting…

When Jewel started garnering attention at the coffeehouse, she didn’t have a manager, agent, or a lawyer. As documented in the book, “Intimated by the executives taking her out for dinner after her Thursday night shows, she went to the library and found a book titled All You Need to Know About the Music Business. It was here that she learned that signing bonuses were really just loans that you have to pay back through your earnings.”

The bottom line is that Jewel realized that if she signed with the record label, not only would it take a long time to pay back the advance, but she would be under a lot of pressure from the record label and they would be calling all the shots on her sound (and her future).

Instead, she made the purposeful decision to turn down the huge signing bonus. Lower earnings on the front end and more on the back end. Since she was still early in her career, she recalled “I had to put myself in an environment and a position to win as a singer-songwriter, and the best way to do that was to be cheap.”

The thinking went, if she didn’t cost the record label that much, they would be less likely to drop her if she wasn’t an immediate hit, and this in turn would provide her the freedom needed to sharpen her craft and pursue something new and exceptional with her music.

She adopted a motto for her intentional approach: “Hardwood grows slowly.” This phrase she learned from her grandmother growing up in Alaska.

Jewel went on to release “Pieces of You,” which eventually became one of the best-selling debut albums of all time, achieving platinum status twelve times. Throughout her career, she showcased her versatility as an artist and stayed true to her authenticity. She’s received numerous Grammy nominations and has been praised for her vocal range and songwriting skills.

So, what the hell does this have to do with selling software to large enterprises while enjoying the work? Quite a bit, actually. Let’s unpack it further.

Obsessing over quality leads to joy in your work

As captured in this definition, “when you concentrate your attention on producing your best possible work, a more humane slowness becomes inevitable,” Newport explains.

A focus on producing high-quality work not only leads to better outcomes, but it also enhances personal satisfaction and engagement with your work.

To be an effective revenue generator you first have to become a quality value creator. This work should be pleasurable, not a pressured, hectic grind. That’s not to say all aspects of it will or should be easy, but it should ultimately be a joyful pursuit. As I’ve also written, a happy seller is an effective seller.

Let’s break down and apply this concept across three horizons:

1. Landing a new role

2. Ramping up in the role

3. Sustaining success in the role

Landing a new role

It’s easy to be cynical about companies in today’s environment. I think it’s healthy to be skeptical and not be too eager to drink the Kool-Aid, but you also need to balance this with a level of (personal) optimism.

When you search for the next environment to ply your trade, do you know what you’re getting yourself into? Are you pushing hard for a hefty compensation package, or are you getting clear about creating autonomy for yourself?

Most sellers I speak with focus heavily on the comp package. But as you learned from Jewel, another path is to “be cheap” to the organization. A lot of sellers focus on selling themselves on the role but don’t do enough due diligence to understand what’s truly expected of them when they get there. There’s a lot of “we’ll figure it out as we go.”

⚡️ Bold move: Make comp the last factor of your decision criteria. Have enough money saved where you’re not under pressure for the first six months to close deals. Get crystal clear on what’s expected of you in the first year and carve out as much autonomy and agency as possible.

This leaves you with ample space and reduced pressure to raise the game to your standards, not the company’s expectations.

Ramping up in the role

When you start out, the key will be equipping yourself with a set of standards that are much higher than the expectations of the company, as I broke down in this lesson.

As a reminder, here’s what that visual looks like:

A common approach at most organizations is to provide some sort of ramp for sellers, typically three months, where there is no expectation of closing new business, but instead, to get onboarded, learn the product, and acclimate to the role.

⚡️ Bold move: When the company is moving slowly, that’s when you want to move fast. It may seem counterintuitive to Slow Productivity and, what I often talk about here in The Purposeful Performer and on LinkedIn, but in many ways, it’s not. Let me explain.

When I joined LivePerson as a new logo hunter on a dedicated Strategic Accounts team with five others (three new hires and two existing sellers), I took full advantage of my “downtime” to ramp up my pipeline. Before even joining the company, I obsessively studied our most innovative customer, which allowed me to formulate a distinct point of view and get hyper-targeted with my account list as I walked in the door.

My mantra at the start was “say yes to everything” because I wasn’t allowing myself to get bogged down by the typical onboarding process that my colleagues were slowly enduring. In my first ninety days, I had already met with Aramark, Facebook, and Apple and launched my open-letter approach to Delta.

I started in January, and by the end of the year, I had closed over $2.3M ARR against my quota of $1.3M ARR. Nobody else on the team was able to hit their number.

Back to Jewel…

When she signed with the record label, she “focused her energy on building a fan base through touring, which she began to do at a relentless clip, taking on a ‘tremendous workload.’ True to her plan, Jewel kept her expenses low. Instead of having a tour bus and a tour manager, she traveled cheap in a rental car and performed without a band.”

As was the case for me and for Jewel, Slow Productivity is not so much about being slow, it’s about a mindset of being highly purposeful with your decisions so you can grow into who you ultimately want to be.

It’s about playing the game by your rules, not those of others.

And it was more fun doing it this way. For both Jewel and me, the joy came from pursuing our craft, not stifled by rigid rules that put pressure on us to be active in ways we knew wouldn’t make an impact.

Sustaining success in the role

Once you make a name for yourself in the organization, you create further freedom and autonomy. Now, the mantra shifts from saying “yes” to everything to “no” and only ruthlessly pursuing opportunities that match criteria important to you.

This is when you can leverage everything that you worked purposefully to build quickly to now move at a more natural (slower) pace:

• A powerful network

• Key internal relationships

• Specific knowledge (like architecting large deals)

• Commission checks to diversify your income streams

Jewel had recorded her first album with the help of Neil Young (her choice, not the record label’s) before she went out on her first tour. As a new songwriter, she was a bit nervous and intimidated to work alongside her musical hero.

But after she returned from her whirlwind tour across college campuses to build a grassroots fan base in a rental car, she gained confidence and found her sound. She then translated all that she had learned and re-recorded a new version of “You Were Meant For Me.” After she released a sultry video for the song, sales exploded. The album went from selling a few thousand copies in the first year to close to a million copies a month.

⚡️ Bold move: As you gain success, reinvent “your sound,” or in other words, create a new role for yourself by cashing in your chips. To repeat big years, you have to write your own plan, not the company.

This will set you up to make joy and working in a way that’s more purposeful at the center of your operations. You can’t help but shine when you’re in a position like that!

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