Learn to sell

From time to time, I get asked for career advice. Sometimes it’s folks looking to get into product management, and others just curious about working in technology generally. I’ve thought a lot about what type of advice I can give that would actually be useful.

A big problem with an awful lot of career advice you hear, particularly in tech circles, is that it’s hopelessly tainted by survivorship bias. Almost all life/career advice from famous rich people is usually useless for this very reason. Beyond that, it seems like the most popular advice you see is “learn to code.” I think this is a mistake, and not very useful for most people. Learning to write code and develop web applications has definitely been a positive in my life, but it’s probably only been marginally advantageous career-wise. I’d certainly encourage anyone to learn, but mostly for personal enrichment, not career advancement.

Instead, here’s my pitch: go do a stint in Sales. If I were early in my career and looking to boost my long-term trajectory, I think is where I would try to start. Even in mid-career, where I am now, it’s something I think about often. More tech professionals should consider it. Hear me out.

Sales really, really matters

When you listen to the tech industry talk about itself (which it does constantly), it would be easy to think that everyone is a developer; or that developers/engineers are the most important people around, and the only ones who really matter. This is really dumb.

In our book on enterprise Product Management, I included this quote from Philip Kotler:

The sales department isn’t the whole company, but the whole company better be the sales department.

I find it remarkable how little the tech world talks about software sales, given how central it is to everything we do. Sales is the whole reason we build anything; it’s how we assign value to what we do. If someone doesn’t trade some value in exchange for your product, then what you have isn’t really worth anything. It doesn’t matter how brilliant your software engineering is if no one buys it.

There are certain swaths of the tech startup world that recoil from Sales. There’s a certain fantasy that exists of “products that sell themselves,” which don’t require a company to invest in either the personnel nor company orientation to serve customers. There’s a reason why non-startups don’t have this attitude: the companies that do never break out of the startup phase. Those companies that see Sales as a grubby and unpleasant chore, rather than what the whole company is about, generally don’t last long.

Fortunately, most healthy software companies see Sales as an absolutely core function, which is why pretty much every one is always hiring good salespeople. For those with a hunger to learn, this provides a terrific opportunity.

Sales gets a bad rap

On the flip side, software sales suffers from a reputation for growth-hackery, spammy tactics that we all hate. If you work in this field, your inbox is probably as full as mine is of irrelevant and annoying spam email from salespeople whose products you don’t care about. It’s a huge turnoff. Trust me – I get it.

But after working with a lot of good enterprise salespeople (as well as some bad ones), one thing I’ve learned is that they also dislike these kinds of “spray and pray” lead-generation tactics. Casting a wide net is simply part of the game, of course, but wasting your prospect’s time is bad selling. Every good sales professional knows this, which is why the best ones put in the time, effort and attention to detail to make their pitches – even the opening ones – as tailored and relevant as possible. That might only mean increasing their response rate from 2% to 3%, but that’s a big lift when you’re talking about warm enterprise software leads.

“Good” sales practices are less widely appreciated because they don’t piss people off and so aren’t constantly discussed. Great salespeople, at every level, are able to contribute value to their company and are quickly recognized as such.

Sales experience is golden

No one is more connected with customers than the folks in Sales, and as such, they gain a great deal of political power. Customer feedback, after all, is worth its weight in gold. Outperforming salespeople are quickly recognized and tend to get a direct line to the most senior executives in the company (at least, in any functional firm). Everyone wants to make that year’s President’s Club.

Another major bonus to consider is that great salespeople have nearly bulletproof job security. The biggest cause of sales personnel attrition is leaving for another company that offers a more lucrative compensation plan. Salespeople who perform are almost never fired, and among the last to be laid off (for obvious reasons). Of course, others leave because they just want a role that’s slower-paced, or simply aren’t good at customer relations (which is a good reason to get out of Sales).

One downside to all that popularity is that good salespeople sometimes find it hard to transition to a different role, because everyone wants them to stay in Sales. This can be overcome, but the pressure is there.

The tradeoff for being such a valuable member of a company is that Sales is really hard work. Everyone knows that Sales is often a high pressure position (get those deals signed before end of quarter!), has a steep learning curve (gotta learn the product fast!) and requires travel. But the thing that scares off most people, I find, is the uncertainty being on a quota compensation plan.

What I wish more people understood was that most quota plans are actually less scary than I, too, used to think, and some can even be tailored for individuals (higher base comp versus commission, etc.). Good sales organizations understand that there are factors beyond any individual’s control, and don’t want to lose good employees; but nevertheless, you have to reward performance. If you’re a high-performer, quota compensation plans can be incredibly lucrative, which is a good enough reason as any to consider a Sales gig.

Those gigs come in all sorts of flavors, but the most common varieties are thus:

Entry level: Lead Development Reps (LDRs). These are the folks doing the hard work of cold calling, sending tons of emails, doing prospect/company research and developing cold leads into warm ones. Typically you have a couple of LDRs assigned to one Account Executive, but often working with a team of others. Good LDRs usually get promoted to Account Executives.

Mid level:

  • Account Executive – this is a fancy title for “seller” that is called an “executive” to puff prospects’ egos. Often, this person takes warm leads from their assigned LDRs and develops a relationship with a prospect to sell their given portfolio. They are the point person in navigating the account relationship towards a deal.
  • Solution Consultant (AKA “Sales Engineer”) – this person assists the Account Exec in doing product demos and working with the prospect’s technical team on finer points of implementation and strategy
  • Solution Architect – this role is more common in larger companies with multiple product portfolios. This person helps the Account Exec and the prospect design more complicated, cross-portfolio solutions that involve a lot of customization and negotiation over lots of different products

For an entry-level candidate, LDR experience can be a trial by fire, but one that gives that person a solid base of experience that they can use. It also tends to pay pretty well – certainly better than the first jobs I did right out of college. If I’d known then what I do now…

For my own part, I thought seriously about going into a seller position back when I was at IBM. A different role opened up first, though, so I took it instead, and that is part of what has led to my development as a Product Manager today. I like this role, and don’t have any plans to do anything different for now; but down the line, who knows? I, like many other PMs I know, am also attracted to sales engineering roles, because it allows us to keep one foot on the technical and strategic side while also working directly with customers, which is often fun.

Bottom line: think about doing Sales, because that’s really where everything starts, and your results are more driven by personal performance than almost anywhere else in a company. Product, Marketing, Customer Success, even Engineering – all of these functions fundamentally derive from what Sales first makes happen, and your sales experience will almost always be considered immensely valuable in those roles down the road.


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