Start by Hiring the Best Leaders

I hired Kelly two companies ago, at BigMachines (later acquired by Oracle), and she is the best person I’ve ever hired. BigMachines made complex sales automation (CPQ – configure, price, quote) software. It was and is a great tool but can be difficult to sell, implement, or even explain. But when the problem is enabling an organization of sales reps to more easily sell something like a pharmaceutical trial, or a rack of servers whose connections to each other are verified, or a frickin’ enormous mining shovel that will be forged, built, and sent to South America, then the solution may have a few moving parts.

A few weeks ago, she gave her notice. It’s given me time to reflect and that’s why I’m writing this article.

My first gig leading a customer success team was at BigMachines. I had never hired anyone before, but I knew from being a sales engineer the traits needed in what I still think is a very similar role. I will never forget that Kelly told me she could be a CSM because she was currently front desk person/clerk at a law firm and was able to get the lawyers there (who were well on in years) to understand and use excel. Sold – you are hired.

When I left to join another startup (SteelBrick, later acquired by Salesforce), Kelly naturally took over the BigMachines team. When I took a role in integration to help our services org find proper homes in the greater Salesforce family, she did it again for the SteelBrick team. I hired her for a third time when I took my current role at G2 Crowd. And now, seven years after I hired her out of her clerk role, she is now leaving to be VP of Customer Success at another startup in our entrepreneurial family. While it makes me sad to not work with her directly anymore, I am over the moon excited for her. She was probably ready to run her own show when she joined me at G2 anyway.

I realize that was a lengthy ode to open with, but my teams’ success has been due in large part in convincing Kelly to join the ride three separate times. So I’ll say the reason our teams have grown, hit and exceeded metrics, and registered the highest in-company NPS scores are for things “we” did – but you get it. She has made me look very smart and competent at work.

Back to hiring – we have always stuck with a few tried-and-true behavioral interview questions. A question about how you saved a customer or brought value by applying something complex you’ve learned. Another essential is if the question-and-answer evolves into a conversation – if the candidate can have a good conversation with me across multiple topics then I feel much better about giving them our biggest customers. Finally, all employees at G2 and our past two start-ups have had to pass an aptitude test before even a phone screen. These three best practices have driven our success in hiring.

Kelly and I know what it’s like to leave a company we love. We’re both start-up folks at heart and given the leadership team we’ve worked with a few times now, these start-ups grow and graduate from being start-ups. The meeting you call to announce your plans to leave is a tough one. I’ve cried each time I have done it, if only because it’s tough for me to grasp how I’ve been granted the opportunities to work with the individuals I have. Others have cried too and I have only recently started to understand the reason why.

We have been privileged with loyalty from many of our team members. That loyalty is a gift, an investment from a team member to a leader, and certainly a risk. It is much easier to float between jobs and companies, but so many have effectively said, “I will follow you and take at least some of your advice, while you try to lead this chunk of our company through hypergrowth”.

None of this is comfortable (or boring! for that matter).

Something that hit me this week is how important it is to balance “sticking up” for a team member while allowing them to cut their teeth. Years ago I made a characteristically unique hire. This woman split her time working for a social media start-up in the Middle East, as well as copywriting and dabbling in politics. Yes, ok, you will now be a CPQ CSM (one of the best I ever hired). Fairly early in her career with us, she said her husband’s entry into the US had been delayed and they needed to settle in Europe to wait it out. I think she thought she’d need to find a new job. She was such a grinder in the role – worked a large portfolio of very diverse (and sometimes challenging) customers, took tons of calls at all hours. Of course I wanted to keep her but I’d never faced a situation like this before. Not afraid to look dumb (from vast experience) I asked the leaders of our company, who are all originally European if we could keep her on. It was a no-brainer across the board to not only do that but fund the move and offer help via immigration connections. Years later she is continuing to advance in her role at the same place.

A more mundane (but still important) example is going to bat for a team member when facing pressure from sales. CSMs ideally work hand-in-glove with their enterprise AE counterparts but conflicts of interest are unavoidable when one role is heavily comped on a single customer, and the other is salaried across a disparate customer portfolio. There is a healthy pressure here that is required for company growth. Kelly and I have spoken to many a salesperson/manager when a rep has asked too much of a CSM (and there is a “too much” even for a company in hyper growth). I think this has meant a lot to our team members. But it would be a disservice to coddle a CSM and prevent him from learning how to fight his own battles. I had a repeat situation between a CSM and AE where I took the above approach but issues continued. So I aligned with the sales leader and we agreed our team members needed to work it out with each other. We quickly reached a resolution lead by the AE and CSM who I think were the better for it.

So, in conclusion, the number one thing to remember if you want to build a first-rate success team is to hire Kelly. Wait, no, hands off! Maybe her name isn’t even Kelly? Ctrl+F replace Kelly with Bob…

There is plenty more to consider how we found ourselves in wildly successful and joy-filled teams. From leadership to the summer interns to those who feed us and clean the office when no one is around – it takes a village. We have always found ourselves in a great village. But for our little patch, we have had to be in turns disciplined and creative in our hiring. And we have loved investing in and encouraging our teams, especially in tough spots so they will perhaps commit and trust that much more in getting the team where it needs to go.


Andrew Stapleton is the Vice President of Customer Success at G2 Crowd and is a guest contributor.

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