Career Life Stories: Dan Portillo, Greylock

From a rapid succession of temp jobs during internet boom to an early hire at Mozilla, Dan Portillo from Greylock talks to us as part of our Career Life Stories series about how he went from startup hopping to becoming a Talent Partner at one of Silicon Valley’s most admired VC firms.

What led you to an early career in recruitment, and can you share a bit about your journey?

Like most people, I got into recruiting by accident. In 1999, at the height of the internet bubble, I decided to take a break from school at UCLA to try and find a job I wasn’t qualified for. One of the companies I had been temping for wanted to bring me on full-time, but I turned them down because I thought I deserved equity (despite basically being an admin). That company went from wanting to hire me to deciding I wasn’t such a good fit for them after all.

When the temp agency, perplexed, brought me in to give me a bit of a slap on the wrist and figure out what happened, I expressed to them my interest in several other startups whose visions were much more aligned with where I thought the market was heading. There just so happened to be a coordinator position available at one of those startups, Zaplet, an internet darling that was growing like crazy. I didn’t know the first thing about recruiting, but I accepted the role and within a couple months I was recruiting for one team and a couple months later I was recruiting for multiple teams, helping them scale from thirty to a couple hundred within the year.

From there, I was hooked on startups. I thought I would be an independent contractor forever – be the first recruiter, build engineering teams, and when companies wanted to hire customer support or sales, I would show myself the door and move onto to the next interesting technical challenge.

That all changed in 2005 when I joined Mozilla along with John Lilly (Mozilla CEO) and Mike Schroepfer (now Facebook CTO). Mozilla, which was about 20 people at the time, had never recruited anyone before, so the opportunity for me was enormous. I fell in love with the company and stayed there for over five years working directly for John and owning the entire employee experience from HR to performance management.

How did you end up in your role as a Talent Partner at Greylock?

I landed at Greylock through a series of introductions over a couple of years. While at Mozilla, Josh McFarland (who I met my very first day at Zaplet), reached out to ask if I would be open to speaking with Greylock. Truthfully, I hadn’t heard of Greylock at the time, so I went to my boss and mentor, John, to see if he could give me any insight. He told me Reid Hoffman, who was a member of our Mozilla Board, knew them well and that I should speak with him. I met with Reid who told me that there was a non-zero chance that he would end up joining them. I was, of course, too embarrassed to ask what “non-zero chance” meant…

For a time, I continued conversations with Greylock but ultimately decided to accept a promotion to the executive team at Mozilla. Not long after this decision, Reid Hoffman announced he was joining Greylock, and within a matter of months John Lilly, my Mozilla boss of five years, announced he was joining Greylock. The following spring, I joined a company I was advising called Rypple. It was a chance for me to expand my skillset. I worked on sales, marketing, product, customer success…you name it.

Roughly 18 months into my Rypple role, I had lunch with John who suggested, once again, I come meet with the folks at Greylock. This time, it was a no-brainer. I’d known Reid and John for a long time, and it ended up being a quick decision to join the team. Hard to believe it’s been seven years already.

What does it mean to be a Talent Partner at a VC firm and specifically at Greylock?

There are different types of Talent Partners. There are some Talent Partners who are focused solely on executive search, and those Partners generally come from careers within executive recruitment firms. There are fewer Talent Partners that have come from the startup side, helping companies scale from the inside. At Greylock, we call the latter Core Talent which focuses on filling university through senior director level positions. In addition, we work hard to ensure our portfolio companies build internal recruiting machines that will scale.

Largely, my team and I focus on three areas which include 1) helping companies operationalize their recruiting efforts, 2) building deep networks—we call them Communities—that will be valuable to us in the long term, and 3) doing whatever we can to support the core business which is investing via introductions to entrepreneurs or through leveraging our networks and recruiting capabilities to tip competitive deals in our favor.

What has been the most surprising aspect about your role on the VC side?

I had a solid network before I came into this role, but within my first year at Greylock my network doubled and within two years, it doubled again. What I’ve come to understand is that recruiting in Silicon Valley is a network business. It’s not just about knowing the right people, but it’s about knowing the right people for a particular problem, and it’s exciting to get to draw those connections.

What is the most unique recruiting challenge you’ve worked on?

One of the most unique and, quite frankly unexpected, recruiting experiences of my career is actually fairly recent. In 2014, I met Todd Park, the then White House CTO and advisor to the President. Over the following year, I had the chance to support Todd and the US Digital Service from afar in my spare time.

In 2015, while deep into my role at Greylock, I was more actively recruited by President Barak Obama and Todd Park to officially join the Digital Service. I knew the leap was inevitable when President Obama shook my hand and said, “Now why can’t you join us?” Greylock was gracious enough to allow me to take a leave of absence to help the government recruit our country’s leading technologists to the government. Talk about a once in a lifetime opportunity!

What personal attributes and professional experience do you look for when you’re hiring for your own team?

The people that have been most successful for me over the years have been hunters. They have been exceptionally good at identifying talent, enticing them to talk, and making strong recommendations for that person on where they could go. They also LOVE it. To this day, after 20 years, I still love sourcing – getting someone on the phone and getting them excited about an opportunity.

They type of people I look for are very candidate driven meaning they invest time in getting to know what each candidate wants out of their career. I don’t want my team recommending ten companies to someone; I want them to fundamentally understand an individual’s skills and passions and then recommend maybe three companies that fit that specific person.

I recently broke my own recruiting cycle record – 15 years from introduction to placement. Recruiting is a very long game, and the people I hire understand that.

What advice do you have for founders with little experience hiring their own team?

First and foremost, you have a to tell a good story. You must be able to articulate…

…who are we?
…why do we exist?
…what is the potential of what we can do?
…why does it matter to you?
…why do we want you? (not the generic you, but you, a specific person)

If you’re a good story-teller and you run a tight process, then you’re going to beat most other startups.

I put together this internal recruiting deck for our seed stage companies here at Greylock which got picked up by Business Insider and has since been viewed over 400,000 times.

There are no shortcuts to recruiting – it takes a lot of very hard work.

How has momentum around diversity and inclusion impacted how you help portfolio companies think about hiring?

Diversity is top of mind for everyone right now. Having companies go through diversity and inclusion is a good exercise for figuring out how different biases might be manifesting themselves throughout the sourcing or interview process.

At Greylock we focus on building top of funnel activities which attract a diverse set of candidates and then frequently assess our decision-making processes. We’re sensitive to presenting our portfolio companies a pool of candidates with diversity among them, but we do not seek to exclusively represent diverse candidates for particular roles.

In your experience, when is appropriate for founders to consider using external recruitment partners vs hiring an internal recruiter or vice versa?

I think it depends on the growth rate of the company. It also depends on how strong the founders are from a recruiting perspective and whether they have robust personal networks. Founders first need to figure out how far their personal networks will get them to project when they’ll need to bring on additional support.

I usually recommend bringing in an internal recruiter sooner than later – preferably full-time but sometimes part-time is more appropriate if there are only a few roles. I tend to recommend brining on agency partners to support the internal effort or for a one-off position.

I try not to have a one-size fits all approach for our portfolio companies. That said, I’m not aware of a single company that felt that started working with a recruiter (whether internal or external) too soon.

As we wrap up, what resources (books, podcasts, blogs, or events) would you recommend to recruiters or others in people-focused roles?

In terms of tools, at Greylock we use LinkedIn and Topfunnel. In terms of reading materials, I recently put together a blog post of useful resources for recruiters which you may find helpful.

Finally, what is the best way for people to connect with you (Twitter, Medium, etc)?

The best way to connect with me is via LinkedIn.

For more Bay Area Career Life stories brought to you by Robert Walters, check out these interviews from other key contributors to the tech ecosystem: Elain Szu from AccelTerence Lim from UdemyAnjali Jameson at Rally Health, and Caroline Ingeborn at Toca Boca.