Hi, I’m Alex Escobar, Head of People and Talent at AppSumo. AppSumo is the leading digital marketplace for entrepreneurs to shop software, digital courses, and other resources for building successful businesses.
Our team has been growing fast these last few months. (In fact, we’re hiring!) One of our latest hires was a Head of Engineering. For context, typical Engineering leadership roles take 6-8 weeks to fill.
From start to finish, my team hired our new Head of Engineering in just 28 days.
Here’s how we did it.
The recruiting game has changed
I began in HR and recruiting 16 years ago at United Airlines. One of my first hires came after months convincing an engineer they should consider leaving their cushy job to come work with us.
Every search begins with a little elbow grease, but back in the day, we had limited tools. LinkedIn was not a widely used tool back then. I spent a lot of time on Monster and Careerbuilder, sifting through the abyss of resumes, hoping my dream candidates would somehow shine through all the irrelevant ones.
Everything about the job was labor intensive.
Fast forward to 2021, things have gotten simpler. We have a recruiting-optimized LinkedIn, with advanced search strings and hiring tools. But with ease comes competition from other recruiters with access to the same tools.
Not to mention, finding the best candidates means looking at profiles instead of resumes. Top talent for a role is usually not looking for a job—which is why hiring often takes multiple months to secure a single new employee.
When your ideal candidate is happy with their current job, those first conversations are like a game of chess. What you say—your next move—can either progress the conversation or create excess
Recruiting off-market talent
AppSumo has many excellent developers on the team. But they needed a leader who could advocate for them in more ways other than just being a good manager. They wanted someone who understood AppSumo’s mission and technology.
Before I joined AppSumo earlier this year, our co-founder Chad served as Interim CTO and Head of Product. Finding a strong leader for Head of Engineering would give Chad time to focus on his priority responsibilities at AppSumo.
So I quickly got to work—meaning research.
Who were the top Heads of Engineering in Austin? Finding the best talent for a role—especially senior roles—is seldom as simple as throwing a position on your Careers page. The best candidates often already have jobs they’re excited about. In those instances, recruiting means tracking down the best candidates and then convincing them that your opportunity is even better than the one they already love.
The Dream Fifteen
My first task was to get hyper-focused about who to contact. I created a list of 15 candidates in the Austin area who I knew checked all the boxes for the person we thought would excel in our open role. The more vetting a recruiter does up front, the less time we have to spend interviewing candidates. From there, I prepared my pitch.
I had to be strategic in my message. An unfortunate stereotype about recruiters on LinkedIn is that we just send the same vague message to hundreds of semi-relevant candidates. That means a cold email or LinkedIn message from a recruiter doesn’t mean anything. To avoid being ignored, each message had to be personal and specific enough for each candidate that they know I’m not a bot.
In other words, all 15 candidates needed to know that AppSumo meant business.
13% response rate
From our Dream Fifteen, two candidates were interested—a 13% response rate.
Among the two candidates was Matt Ward. Matt met all the requirements we were looking for in a Head of Engineering, particularly a background in multiple director-level engineering roles at recognized companies like Procore, Amazon, and Nordstrom.
But beyond his relevant titles and experience, I also learned that Matt had experience successfully managing teams of developers through an IPO—a core skill we were looking for. To top it off, he was passionate about diversifying engineering talent.
I quickly scheduled a call with Matt to discuss our current leadership needs and long-term goals for the department. We spent 45 minutes speaking about everything I knew from only two weeks of being with the company.
From there, we were off to the races. With everything said and done, we were able to close the role with Matt as our leader of choice, and we cannot be more excited about him joining the team. It took 28 days total.
How did we get to the finish line so quickly?
Here are my thoughts on what I feel were the impactors to our success with Matt:
HR has its stigma, and I have been one to carry that stick when I talk about policy and process. But nothing will ever beat being honest and transparent when you need to get things done.
I was honest with Matt when I told him we had some things that needed to be fixed. Our team needed a strong leader who wasn’t afraid to advocate for them. I told him the stories of the people on the team. He wanted to know exactly what he was getting himself into, and I wanted to be totally transparent.
Every detail matters, even if it’s the ugly truth. This isn’t airing our dirty laundry, it’s preparing your candidates to start thinking innovatively in the role and picturing the change they can bring.
Not every candidate has the stomach or desire to get their hands dirty. But if I was going to make sure we landed Matt, he had to know the good and the bad.
The rest of the interviewing team —Chad (CTO), Ayman (CEO), Noah (Chief Sumo), and two leads on the Engineering team: Eric and Justin—didn’t hold back either. .
Now don’t get me wrong, there is a fine line between transparency and giving too much information early on. There should be a balance between empowering candidates and demotivating them with analysis paralysis. Find the things that people care about, and craft your pitch around that. You’ll come off as authentic and caring about both your teams and candidates.
In the tech industry, you constantly hear horror stories of candidates being treated poorly and only given enough information to create a facade of a not-so-perfect culture. To successfully recruit candidates, practice the company values that you’re also preaching.
Even if you don’t move forward with someone, you will leave an impression on them to refer someone else or consider you again in the future.
2. KISS (keep it simple, stupid)
I have worked for the biggest names in tech, and no matter how big or small your company is, red tape will never help you in recruiting.
Some leaders I’ve worked for liked adding bows to the process to make it seem efficient, but all it did was slow down the chance of closing candidates quickly.
At Apple, I learned how being efficient and clearing the road of any obstacles makes it easier to make decisions quickly. That means you can spend more time confidently making decisions and acting on them.
Within the first two weeks of my role at AppSumo, I got to work on clearing the road. We didn’t necessarily have a ton of processes for recruiting, but we didn’t have a vision of what we wanted to accomplish. Now we have a 4-step process, and it runs like a well-oiled machine. We removed the barriers that create bottlenecks and now we can make decisions on candidates quickly.
One of the biggest takeaways from our 4-step process is keeping diversity a top priority by holding each other accountable.
One of our company values is Keep Sumo Humble. That means calling out bias when we see it. If a hiring manager tends to lean to one type of culture based on their upbringing, we call it out. Our goal is to make sure that everyone has an equal opportunity, no matter who they are.
Having the right tools like LinkedIn, Greenhouse, and an HRIS to onboard is essential. Onboarding doesn’t start when a new hire starts on the first day. It happens the minute the recruiter reaches out to the candidate.
Tracking every conversation in a good ATS with intelligence to keep your teams accountable on time frames is vital.
As the saying goes, “cash is king,” but for us on the Taco Recruiting team, “time is king.” Everything you spend your time on will either help you move faster later—or slow you down.
Use tools to your advantage. We use Calendly for our interview scheduling tool, Glassdoor for our ATS, and of course, LinkedIn for one of our sourcing platforms.
I am constantly thinking of ways to speed up our process to compete with the FAANG companies. We are small, but mighty. To catch the attention of people like Matt, we have to use our tools efficiently.
4. Close internal partnerships
This is a term that most people want but have a hard time understanding. I tell my team all the time: you are not an order taker. You are a partner, and your knowledge and experience matter. Our recruiters deal with the moving market every single day. Their ears are to the floor across industries and competitors.
But all that external knowledge can’t be used without understanding the core needs within your own organization. Recruiters should be an extension of the departments they support, covering the same things a hiring manager would in an interview.
I care more about the hiring team making sure a candidate is a culture fit than a technical fit. The only way to accomplish that is by learning the business. It requires hearing the stories of our team members, sharing their experiences, and learning about each other.
Maintain strong internal relationships. Our recruiters spend a minimum of one hour with each leader weekly talking through the progression of the open jobs. The goal is not updates but having an open dialogue to build a deeper understanding of hiring needs and market challenges.
Transparency as a recruiting tool
In the end, it wasn’t our process that convinced Matt to join the team. It was our team’s stories and vision. He felt confident in our ability to speak honestly. And he caught the vision for where AppSumo’s needs and his specialized skillset could intersect to build amazing things in the future.
Welcome to AppSumo, Matt!
If you’re curious about the roles we’re hiring for, I’d invite you to check out appsumo.com/careers.