The Good vs. The Bad of SF Bay Area tech sales

Productivity 5 min read

As someone who’s worked in a variety of sales roles, I consider myself a critical observer and participant of the San Francisco/Silicon Valley sales scene. I’ve seen both the good and the bad of the very connected, very competitive sales landscape that this area seems to be known for.

Below are “The Good,” “The Bad,” and “The Questionable” areas of tech sales in the SF Bay Area that I’ve experienced:

The questionable: salespeople

San Francisco attracts a specific type of salesperson: someone that is financially motivated (you do have to afford living here) and excited to work for a hot startup but lacks the technical experience that would qualify him or her for other roles.

This was me circa 2008. Those who are financially motivated but lack technical experience compose a motley crew of salespeople with varied, sordid backgrounds. There’s no standard education, work experience, personality traits or combination thereof that guarantees your success. Books have been written on the model salesperson, but I don’t think one really exists. Day-to-day, all that matters is results and that makes for some questionable personalities.

You’re only as good as your next closed deal

The Bad: sales meetups, conferences, and “networking”

Not worth it. Sales should be about finding and nurturing qualified leads, and what is the percentage of relevant, timely leads for your business that you’ll find at a given sales happy hour? 2%? Salespeople love to socialize (drink), but this is one part of the scene that I find takes up a lot of time and attention, but with very few tangible results. Networking has its benefits and there’s nothing like human interaction, but I doubt you’re optimizing your time by chatting up your lovely contemporaries over coffee-infused beer.

Say “no” to happy hours

The Bad: sales management

Sales is an atypical space in terms of career growth because the best way to “move up” is to sell more, rather than climbing the ladder to Sales Manager, VP of Sales, etc. I’ve found that the people who love sales and do it exceptionally well tend not to become managers.

Managing salespeople is a whole ‘nother ballgame. Because of this, a lot of people who manage sales teams tend to be average salespeople promoted willingly into a management role. Did I stutter? If your manager is so great at selling, why is he managing? Props to the few amazing salespeople out there who are also great managers, you deserve applause. This happens pretty rarely because the potential financial upside is basically infinite for a good salesperson to stay in sales.

My #1 gripe with sales management: “training” salespeople to be clones. There’s really no need to give clients and the general public more reasons to have a negative opinion of salespeople, but when reps are forced to act, talk, look, and sell in exactly the same way, it just screams fakeness and results in a lot of micromanaging (managers listening in on calls, etc).

The sales strategy that worked for one person won’t work for every salesperson on the team, and I prefer to cultivate meaningful relationships with my clients which I can’t have if I’m acting out a script. You’re done if the prospect catches a whiff of anything other than your genuine self.

Master your product and ditch the script

The Good: tech giants

At larger, established companies with “strong” sales cultures in the Bay Area, the setup for individual salespeople is catered to your success, assuming they’ve scaled appropriately.

It’s a great place to jumpstart your career, since having a big name company on your resume is a nice stamp of approval, and the training you’ll receive at these structured tech giants is invaluable. A strong, proven product and good brand recognition means you also have a lot going for you off the bat that will make your job easier.

If you’re considering entering sales at a larger company, interview a salesperson there to get the scoop first, to make sure they’ve scaled properly, and that you’re not walking in to a hyper-competitive, overcrowded sales department. Assuming everything checks out, this is a great opportunity.

Tech giants are great for early career training AND accelerating your career

The Bad: startups

This might seem ironic, given that I do sales at a startup, but I do not recommend doing sales at a small startup early on in your career. You need to get your ass kicked up and down the street before you’re capable of helping an early-stage startup. Large companies are better for the kind of bootcamp sales training you need early on.

At startups, unless you are completely comfortable with ambiguity, setting up your own processes, and possibly having to discover that the startup/product is just not ready for a sales team at all, you will be going down a difficult road. There are only a few reasons why this would be a good idea:

  1. You are interested in building up a lot of adjacent skills (marketing, operations, product development, customer support). Most salespeople I know are not very interested in this, even though they should be.
  2. You have a lot of faith in the product and its future success and want to get in early for the potential financial benefit down the road.

For number 2, keep in mind that the potential amount of money you can make year to year at a startup is generally lower (unless the company is an instant, wild success), because even if you work really hard you are working with some limitations when it comes to product development, support capability, and brand recognition.

You’ll have to spend time wearing other hats outside your core duties as well (Account Management for your own clients, etc). This financial downside can be balanced by substantial equity, which, especially given the stage at which startups start looking for salespeople, is quite rare.

Be prepared for the long game

The Good: learning curve

Sales is a great way to have a job that is exciting and different every day, because you’ll constantly be learning. Once you’ve gotten past the initial hump of figuring out your product and owning your own style and what works for you, you’ll have a blast closing deals and sharing your expertise.

The sales team is in the middle of everything, so open yourself up to the experience and wisdom around you from your cohorts in engineering, marketing, customer support, and c-suite leaders. What they know will help you sell better. Your feedback will help them be better as well. This is the main value-add you can provide in addition to revenue.

Bring in the money and help refine the product; you’re more than a salesperson

Final tally

2 “Good,” 3 “Bad,” and 1 big one that’s “Questionable.” This mixed final score represents my own sales experience pretty well, and I’ll continue to write about things I’ve learned (and continue to learn) along the way.

Let me know your own assessment of each of these fields or ones I’ve missed, and any topics you want me to write about. Next up will be sales salaries (what to look for, what’s expected, and so on).

Thanks for reading!

Josh Gillespie

Josh Gillespie Director of Enterprise Sales at PandaDoc

Josh is the Director of Enterprise Sales at PandaDoc. When he's not closing large deals or working on complex SaaS implementations, you'll find him either on the basketball court or rocking the salsa dance floor with his wife.

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