Lists of Must Reads From the Most Talented Tech Operators in Our Network

Lists of Must Reads From the Most Talented Tech Operators in Our Network

Dig into seven reading lists curated by our network of operators and experts, as they recommend must-reads for their disciplines: product, sales, recruiting, marketing, management, engineering and more.

This year, we’ve featured some commanding voices on the Review, from household names like Instagram’s Mike Krieger and Reddit’s Alexis Ohanian to stars-on-the-rise like Atlassian’s Aubrey Blanche and LaunchDarkly’s Edith Harbaugh. (Stay tuned for our 30 best pieces of advice in 2017 from these operators and more next month.)

The Review was built on the premise that there’s more wisdom outside one’s walls than within them — and that’s the very reason why we continue to search far and wide to feature technologists beyond our community. We frequently rely on research and referrals, but this year, that “room” grew substantially through several First Round initiatives:

  • We launched Co-ops, small groups of leaders working in tech – in functional areas like product or verticals like healthcare – who advise and invest in founders at the earliest stage.
  • Our mentorship program paired over 75 seasoned operators in product, sales, design and more with early-stage founders and rising stars in their same functional expertise. Mentors hailed from Airbnb to Zenefits, and from Nerdwallet to Coinbase.
  • Inspired by Associate Product Manager programs, we built our Product Program. Over three months, 17 product leaders from Betterment, Flatiron Health, Classpass and more taught masterclasses in their specific speciality to the next generation of remarkable PMs.
  • And finally, we launched First Search, the largest database of curated, high-quality advice for building startups ever created. We vetted, tagged and organized 10,000+ articles about every facet of company-building, written by the best minds in tech. First Search also showcases reading lists curated by experts and a featured advice section — all to make it easier for startups to find the information they need right when they need it.

This last endeavor is an incredible extension of The Review, especially in its goal to gather and share all the valuable company-building advice out there. So, without further ado, we’d like to feature some of the best advice across a range of disciplines — product, sales, recruiting, marketing, management and engineering — from voices that have grown stronger as our “room” has expanded. As part of First Search, we asked them to create lists — startup syllabi, so to speak — of essential reading that’s played a role in getting them to where they are today.

We’re proud to feature seven curated lists — and honored to be featured on some of them. As you set goals for 2018, give them a read. If there’s more you want to learn, there’s much more where that came from here. We hope you enjoy!

Max Mullen — Co-founder of Instacart

On his First Search list, Mullen assembled his must reads for teams growing consumer products. Included is Anu Hariharan’s guide to setting up, staffing and scaling a growth program, Sarah Tavel’s post on user engagement and Casey Winters’ article on why onboarding is the most crucial part of a growth strategy. Mullen is Product Co-op partner and you can find the rest of his top picks on consumer products here.

As a preview, here’s one tactic from a First Round Review article that he recommends that features Meenal Balar, Facebook's early growth leader turned VP Marketing at Remind:

Follow these four steps for sustained growth.

Growth isn't just about user acquisition — in fact, that's just the first of four steps to real, meaningful expansion. Here's the progression every company should be looking for according to Balar:

  • Acquisition: How do you get people in the door?
  • Activation: How do you get them to start using your product?
  • Engagement: How do you keep them using the product and make them willing to come back?
  • Virality: How do you turn engagement into people inviting others to join them using your product?

Each of these steps is multi-dimensional. When you break acquisition down, for instance, you need to think about product discovery, app installations, pricing considerations, etc. “Acquisition is largely about understanding how people discover and share, and mapping your product tactics to match the specific behavior you want to be driving,” said Balar. Similarly, activation requires extensive usability testing and investigation into user friction both inside and outside your product. Why do people come back a second or third time? Juice those attributes to retain even more new users. The more users you activate, the more you can engage — and that's when things really start to take off.

Julie Sommerville, Director of Engineering at Blue Apron

When engineering leader Julie Sommerville was at Business Insider, she rose through the ranks, starting as a developer, then was promoted to Software Architect, later became a Director of Backend Engineering and left as its VP of Eng. All the more reason to give credence to her must reads for new and experienced engineering leaders. Some of the great picks on her First Search list include: Rands’ framework for 1:1s and Jason Lizka’s smart juxtaposition of good tech leads and bad tech leads.

Sommerville also chose to add in Camille Fournier’s wise observations on when managers get stuck — when they fail to manage down, fail to manage sideways or fail to manage up. Here’s an excerpt that looks into one of those scenarios:

Scenario 1: You aren’t actually scaling yourself effectively, aka, failing to manage down.

You may think that you’re handling your team well, but when you look at your schedule, you’re working nights and weekends and then some to juggle all of the new tasks that managing a team entails. Sure, there are some companies which expect that from everyone, but it’s rarely a sign that you’re using your time effectively. Look at your team. Is it a well-oiled machine? Do you feel like the team is able to operate independently, get things done, without you micromanaging every detail? If not, you’re probably stuck on the basic needs of your current job. Some examples of this include:

  • Can’t delegate. Look at all hands-on tasks you own, and ask yourself whether you are the only person who could be completing these tasks, or whether you could assign them to another senior engineer. If you are spending a lot of your time doing hands-on work that someone else could be doing, you probably aren’t delegating effectively.
  • Not training your team. If there are too many tasks that only you can complete, you have made yourself a key dependency for your team. Who are your potential successors, and have you spent time training them on the things only you can do?
  • Not enough attention to the process. Is your team drowning in alerts with no end in sight? Why haven’t you spent the time to allocate people to fix that? Have you spent time paying attention to the way work is assigned in your team? Do you actively participate in the planning process? When was the last time you tried changing it to see how it could improve? Process is part of your life now, and you need to tend to it.
  • Won’t say no. If your team is completely overwhelmed with work, well, it’s partially your fault. You are the manager, and you are the person who is responsible for pushing back on the work commitments for the team.

Keith Cowing — Director of Product Management at Flatiron

Keith Cowing crystallized his First Search list on measuring success down to three outstanding reads. Making the list includes Tomasz Tonguz’s most important metrics for startups and David Skok’s guide to measuring and improving what matters. Cowing is one of the product leaders who taught in the Product Program — you can see the rest of his list of reads here.

To get a peek, here’s a tactical excerpt from a post Cowing recommends on how to keep score. It’s from “The 4 Disciplines of Execution,” a blog written by Sean Covey, Chris McChesney, and Jim Huling:

Build a player’s scoreboard.

The scoreboard that will drive the highest level of engagement with your team is one designed solely for (and often by) the players. This “players’ scoreboard” is quite different from the complex coach’s scoreboard that leaders love to create. It must be simple, so simple that members of the team can determine instantly if they are winning or losing.

Why does this matter? If the scoreboard isn’t clear, the game you want people to play will be abandoned in the whirlwind of other activities. And if your team doesn’t know whether or not they are winning the game, they are probably on their way to losing.

Discipline 3: Keep a Compelling Scoreboard asks you to create a scoreboard with a single purpose: to motivate the players to win.

When you and your team design this type of scoreboard, it will have these unique characteristics:

  • It’s simple – so simple that everyone on the team understands it.
  • It’s complete – it shows both the lag measure results and the lead measures that are driving them.
  • It’s visible – displayed publicly for the team, and others, to see easily.
  • It’s compelling – any member of the team can easily tell if you are winning or losing.

The highest level of performance always comes from people who are emotionally engaged and the highest level of engagement comes from knowing the score—that is, if people know whether they are winning or losing. It’s that simple.

Dhiraj Singh — ‎Director of Commercial Sales and Sales Development at MemSQL

As a sales leader and former founder, Dhiraj knows how to generate momentum in a business. In his First Search list, he shares his go-to reads for sales executives. A few that made the cut: Jocelyn Goldfein’s top questions to ask throughout the selling/buying process and Brendan Cournoyer’s post on the three “levels of pain” to know during the qualification process.

Singh included a few First Round Review articles (thanks!) — here’s a deep-dive into one of them by Pete Kazanjy on the anatomy of the perfect sales hiring process.

Integrate this criteria into your sales hiring profile.

Not to be confused with a job description, your hiring profile is a set of personal and professional attributes that define your ideal hire. Kazanjy used this framework to grow and refine the sales org at his company TalentBin, and later to expand that to thousands of reps at Monster post-acquisition. So, he now says with some conviction: your sales staffing should have the same rigor as your engineering staffing.

Here are some red flags and green-light characteristics to look out for when evaluating the professional characteristics of salespeople. First Kazanjy starts with the red flags, because he’s seen and made too many mistakes when looking for the right professional experience.

  • Industry Focus: Just because someone sold human resources software before doesn't mean they can sell all HR and recruiting software. One product may focus on sourcing great candidates while another might be about employee performance management. The sales cycle, tempo and value propositions are completely different. So, when it comes to industry focus, look for people who have sold to the same decision makers your org sells to at a similar price point and budgetary cadence.
  • Role Focus: A candidate may have worked in sales, but if they were an account manager tending existing customers, they may not be cut out to be an account executive acquiring new business. Just because someone has made 80 sales calls a day in a prior job doesn't mean they can demo and close. Make sure candidates have the expertise you need.
  • Sales Cycle Mismatch: Ignore sales cycle tempo at your peril. If your solution requires a long sales cycle, you don't want to hire someone who's used to one-call closes. They won't have the cat-herding mentality it takes.
  • Industry Bellwethers: Be wary of pulling staff out of the big companies, the monoliths of your space that you hope to eclipse. These reps work with established marketing orgs that drive lead gen and handle existing contracts that are largely on cruise control. They won't have these luxuries at your company, and that is often a deal breaker.

Now that you know where to exercise caution, here are some professional characteristics that Kazanjy suggests to prioritize:

  • Mid-stage startup experience: Look for orgs in your space that have hit “escape velocity,” i.e. sales staffs that are looking to jump onto their next rocket ship. They just finished selling something novel and probably have the skills to do it again. So, let's say you're a new entrant to the recruiting market like Greenhouse or Lever, you may want to pull people out of Jobvite.
  • Your customers: If you sell IT infrastructure, the in-house IT admins who implement and administer your solutions know your problem space backwards and forwards. Familiarity with the industry isn't enough, of course, but paired with other qualities, this brand of subject-matter expertise can be gold.
  • Podium-toppers: Find people who have artifacts of the type of achievement you're looking for: quota attainment, activity metrics, etc. Note that salespeople are used to, well, selling — so don't get spun. I've seen enough embellished titles and self-reported resume gold stars to last a career. You need to ask for actual proof — screenshots of activity graphs and leaderboards directly from their org's CRM, for example. If you're lucky, some of these screenshots will show both where your candidate landed on the leaderboard and the names of the other high-rankers.
  • Rolodex power: The notion of hiring a sales rep for their connections is dying — it may already be dead. You can source would-be accounts from LinkedIn, or other sources, so there's no need to hire for a rolodex if the candidate is missing out on other traits. That said, staff with a lot of existing relationships can be helpful. This should be the lowest-priority quality you look for (by far), but it's certainly a nice to have if you're pressed to hire someone more senior.

Nikita Dyer — Product Lead at Trello

In Nikita’s First Search list, she assembled her favorite reads on product and leadership. A few notable standouts: a concise, exemplary outline of values around building product by Heroku co-founder Adam Wiggins and Henrik Kniberg’s deconstruction of MVPs. You can see the rest of her list here.

To take a closer look at another recommended read from Dyer, here’s a snapshot of one tactic from a Review article featuring former Yammer CTO and Abl Schools founder Adam Pisoni and General Stanley McChrystal:

Employ a hive mind to combine strategy and execution.

General McChrystal’s forces came to realize that the only way to move as fast as their enemy was to empower people on the front lines to make decisions as quickly as they could learn new information. But how do you do this when leaders still believe the people on the front lines don’t have enough information to make the right decisions? By cultivating a shared consciousness. This means getting to a point where you trust almost anyone to make decisions on their own because you believe they have the same information and objectives you do.

One tactic that McChrystal employed helped sidestep the lengthy game of telephone that results from information cascading and rising through the chain of command. His solution to this problem is to combine the process of talking about strategy with the communication of that strategy to hundreds or thousands of people. While he was active in the military, they did this with a daily, large, inclusive 90-minute strategy meeting with leaders and soldiers from across the various branches of the military as well as people from all the branches of homeland security.

In this well-choreographed meeting, there might be a hundred people in the room and thousands of people listening in on a call. Astoundingly, any of the thousands of people dialed in could speak at any time! McChrystal would be the first to admit it was a long process getting to where this worked at scale, but the end result was a hive mind that ensured everyone was acting with the same information and could be trusted and empowered.

“The wisest decisions are made by those closest to the problem — regardless of their seniority.” - General McChrystal

Tammy Han, Talent at First Round

Anyone who has crossed paths with Tammy Han knows that she always has a resource ready to help guide founders and teams with their recruiting needs. On her First Search list, she includes some of the articles she most frequently sends to First Round founders on the topic of finding and hiring top talent. Included on her list is Triplebyte’s guide to hiring engineers and Jose Guardado’s analysis of the true cost of startup recruiting.

Given her years of steadfast support of First Round founders, we’re partial to Han’s own advice, which we outline in our interview of her here. Here’s one highlight from the post:

Make recruiting an act of qualification, not an act of disqualification.

One of the findings in First Round’s 2017 State of Startups report was that hiring the right people tops the list of founder concerns. This doesn’t surprise Han, who works with startup founders looking to hire and candidates looking — or in most cases not, actually — to get hired.

She warns job candidates to beware brand-name bias, scale their search realistically and never say no to a job you haven't been offered. Create and return to a decision matrix (template below). For startups who are hiring, she advises them to inquire about candidates’ motivations directly, not to be afraid to talk money upfront and, of course, be diligent about the candidates they interview. It’s not uncommon in today’s market for an early-stage startup to interview someone from a big name like Google and Facebook — candidates who are likely well paid and enjoying meaty titles and workplace amenities. “You shouldn’t make snap judgments and disqualify purely based off of resume alone, nor should you allow yourself to be intimidated by their recent big company experience,” Han says. “If you are stepping back and not competing — that's another problem that you need to fix.”

Brian Magida — Director of Marketing at Warby Parker

On his First Search list, Magida built his must-read list so that others can stock up on their marketing analytics know-how. Topping the list are two pieces of advice from Simo Ahava’s blog — the first on cross-domain tracking and the second on referral problems on single-page sites. Magida has been a two-time mentor in our mentorship program — you can find the rest of his top picks on marketing analytics here.

Let’s take a look at an excerpted tactic from one of his other selections, an article by Avinash Kaushik on digital marketing analytics:

Design a well-structured digital marketing and measurement model.

The root cause of failure in most digital marketing campaigns is not the lack of creativity in the banner ad or TV spot or the sexiness of the website. It is not even (often) the people involved. It is quite simply the lack of structured thinking about what the real purpose of the campaign is and a lack of an objective set of measures with which to identify success or failure.

I've developed the Digital Marketing & Measurement Model as a simple, structured, five step process to infuse this much needed thinking. Here is what each step in the process helps accomplish:

  • Step one is to force us to identify the business objectives upfront and set the broadest parameters for the work we are doing. Sr. Executives play a key role in this step.
  • Step two is to identify crisp goals for each business objective. Executives lead the discussion, you’ll play a contributing role.
  • Step three is to write down the key performance indicators. You’ll lead the work in this step, in partnership with a “data person” if you have one.
  • Step four is to set the parameters for success upfront by identifying targets for each KPI. Organization leaders play a key role here, with input from Marketing and Finance.
  • Step five, finally, is to identify the segments of people / behavior / outcomes that we’ll analyze to understand why we succeed or failed.

Simple, right? It is harder than you might think, “soft” work always is. Before we go into each step in detail I want to share something extremely critical. The scope/breadth the model has to cover.

A complete, and competent, Digital Marketing & Measurement Model will focus on three key areas of your marketing, and in each answer the cluster of questions provided:

  • Acquisition. How are you anticipating acquiring traffic for your website / YT video / whatever else you are creating? Did you cover all three components of successful acquisition: Earned, Owned, Paid media? How would you prioritize each? Where are you spending most of your efforts?
  • Behavior. What is the behavior you are expecting when people arrive? What pages should they see? What videos should they watch? Should they visit repeatedly? Are there certain actions they should take? What is unique about your effort that ties to an optimal experience for a customer?
  • Outcomes. What outcomes signify value delivered to the business bottom-line? A download? A phone call to your call center? A qualified online lead? Signing up for email promotions? People buying your product / services ? A 95% task completion rate? A 10 point lift in brand perception?

These are only seven of the dozens of expert-curated lists currently on First Search — and more are added every week. Would you like to see articles on First Search or perhaps curate a list? Tell us more here.

Photography from De Agostini/De Agostini Editorial/Getty Images.