First Quarter: Lessons Learned

Here we are, a full quarter after transitioning from Product to Sales. It hasn’t been perfect, but I’ve enjoyed it immensely and learned a ton. I’m still a Product Guy, so I thought I’d dust off the old PM hat and write a lesson’s learned doc. Enjoy!

No one likes salespeople

I know — shocking, right? Prospects know this, salespeople know this, and the industry knows this. When thinking of salespeople (or salesmen specifically), we all have the same images of a Wall Street type in an expensive suit and plastic smile, some dirtbag in a plaid jacket selling cars, or worse. Every book on sales spends time explaining that sales isn’t about screwing over customers (at least not anymore). It’s an unofficial rule of getting a sales book published — the author must specifically mention how modern sales is not like Glengarry Glen Ross. Refuting the sleazy-salesman trope has become a trope unto itself. And yet, the cultural norm persists.

So, I knew what I was getting into. However, I had an ace up my sleeve — no one likes PMs, either. I’m used to being in a role where one of the keys to success is to not act like you’re doing the job you’re doing. To be successful in either role, you need to be both likable and knowledgeable. To quote our principle investor, “Buying is EMOTIONAL. People buy from people they like, from people they perceive to understand their need…” It stands to reason that if salespeople are disliked in general, being the exception to the rule is very powerful. Successful PMs and salespeople are helpful consultants. We’re not trying to manipulate people into doing what we want, we’re trying to facilitate people getting what they want.

I like to think of myself like Happy Gilmore. He excelled at golf, but he wasn’t a golfer — he was a hockey player whose skills made him great at another sport. I’m not really a sales guy, I just happen to be selling — I’m a product guy whose skills makes me… well, we’ll see.

But beyond the issue of prospects and the population at large not particularly liking salespeople in general, the tech sales industry is moving to a more consultative selling strategy. For a recent example, consider that Microsoft just laid off a significant number of people in their Sales org because they were primarily focused on relationship management over subject matter expertise (see Problem 2 of Fred Baumhardt’s article). Product/project managers face a similar problem. Engineers aren’t going to listen to or respect a PM who merely manages the schedule — they need to actually know what they’re talking about. Luckily, I’m selling PM software that I helped design and build, so I’m pretty sure I’ve got this part covered.

The new price of failure

There is no such thing as failure, only learning. -Tony Robbins (and like every other product management guru out there)

Product Management thought leadership has mastered the art of redefining failure into success. I mean sure, they’ll hit easy targets like SMALT, but in general the theme is how failure isn’t really failure, it’s valuable feedback. Your fancy new feature isn’t being used? People hate the new UI? That’s ok! You’ve taken measurements, run your analytics, and iterated. You learned so much! You’ll fail fast and often ad infinitum until you IPO or go out of business.

Failure in Sales is quite different and very direct. If you do not sell, you do not get paid. The end.

Coming from the fluffy world of Product Management, Sales feels like mercenary work. I loved my Product team at LiquidPlanner. I wanted them to do well because they’re awesome and we were all working toward a common goal: building the best product for the right people. I learned from them every day, and hopefully they learned from me. We pushed each other and did great things together, and I can’t really point to a single thing I did — it was all we.

In Sales, I have a team that I like and respect, but I don’t think about their success very much except in the abstract. Maybe that’s not quite true, I also think about their success when I think about how to beat them. Their success isn’t my success; if they don’t sell, they’ll leave or be replaced. I have a boss who is a good dude and I’ve learned a ton from him, but he isn’t really who I report to.

My team is me; my boss is my quota.

It’s been sobering and a focusing factor for what my role is and how I fit into the company. Is this a good or bad thing? I’m not sure. Seems more honest about the nature of the employee/employer relationship, at least. Success = paycheck is the type of clean metric I would have killed for in Product, because as hard as it is to explicitly fail in product, it felt pretty hard to explicitly succeed, too. If we built something that got positive feedback, did it translate to increased new revenue? To increased retention? The closest we got is “we think so…”

Between Product and Sales, I’m not sure which framework is better.

Questions from my team

I thought I’d wrap up with a couple of questions I’ve gotten from people about the transition and the answers I gave them.

Question: What was your biggest surprise about transferring to Sales after running the Product team?

Answer: I had no idea how useless most of the information I gave to the Sales team was.

This was asked by one of the more-seasoned salesmen on my new team a couple of months in, and I laughed when I landed on the answer. Product is all about learning, as it should be. Even if information doesn’t have an immediate and direct effect on your job as a Product Manager, having a large pool of information to draw from is essential to maintaining a global perspective and, ultimately, build a better product.

Sales has gotten me to focus on pragmatic points of the job: how does this information change the way I do my job? If the answer is that it doesn’t, it’s not particularly useful. It was funny to see the new head of product delivering information to Sales and thinking “I kinda don’t care about any of this…” It’s not a knock against him — he’s probably better than I was — but it’s just a completely different mindset. This will be hugely important if/when I go back to product — figuring out how to frame new the information/feature as a change agent to the specific audience. Come to think of it, it’s also hugely important in my current role.

Question: Did you think this job would be harder or easier than it is?

Answer: Selling is easier than I thought, being in Sales is harder.

When I took the job, I thought it would be a huge challenge to learn how to sell, and hone that skill to excel in the role. I’m not saying I’m the best salesman in the world, but I took to it faster than I thought I would — turns out, all that jazz about transferable skillsets in my last post came through.

However, the highs and lows are intense. I naively thought that if I was a consistently great salesman, I’d consistently hit great numbers. In reality, there’s a lot of variance, which often has nothing to do with me. One moment I’m on top of the world from closing a deal, the next I see a mortgage-payment’s worth of commission dissipate for reasons out of my control (customer loses budget, new VP puts the kibosh on the deal, etc.). Maybe the worst, though, is when prospects just go dark. Ghosting isn’t just for Tinder.

It’s rough on the ego — but that’s probably a good thing for me.

In closing…

It’s been a great first few months in Sales, and I’m able to say I’m totally succeeding if we use my old Product success metrics — I’m sure the Sales metrics will catch up soon enough.

Any thoughts? I’d love to hear them. Hit me up at or connect with me on LinkedIn.

Kayvon Ghaffari is an Account Executive at LiquidPlanner. He enjoys behavioral economics, disruptive innovation, and psychologically satisfying third items.