Selling Diversity

The Silicon Valley Glass Ceiling

(originally published April 2017 on Word Press)

Over the past few weeks I have been through the entire interview process for a senior enterprise account executive at Slack, including the penultimate request for references. The references were contacted for availability but those conversations never scheduled. After a number of days of growing anxiety I was finally able to connect with the internal recruiter for a status update call, which she had previously punted on, twice. They had decided to pass. The recruiter confessed she was quite taken aback by this turn of events. She had been quite wonderful throughout the process and this was evidently hard on her, I don’t believe she has ever had to make this call so late in the process.

I have been through this 3 previous times when interviewing with blue chip, “It” companies. “It” companies are those on the ascendancy at any specific point in tech history. High growth, category defining companies where people go to build careers, fortunes, and do great work. Salesforce late 2000s, Amazon Web Services (AWS) early-mid 2010’s, Slack now.

When you make it into the inner depths of these interviews the decision almost always hinges on a personal preference question in the hiring manager’s mind; “would I want to have a beer (or mimosa) with this person?” I was born and raised in Nairobi, a bold, confident, articulate black man, where would you place your bet?

Hence this retrospective.

The Data

I interviewed at Salesforce in 2011, AWS in 2013, and Slack in 2017.

One common denominator with all these interviews was every single person I encountered was white. The other common factor across all 3? I never got an offer. Coincidence or correlation?

In my 14 year technology sales career in Silicon Valley I have met 100s of sales people, only 3 of whom were black and 2 hispanic. Pointedly, one of those 3 got me that AWS interview. Shout out to JD. We had been colleagues at Oracle. He had managed to slip into AWS early in their San Francisco expansion just before things normalized.

The Me Variable

In my most recent role I spent 3 years selling into a complex, dynamic, and challenging sales environment. Selling newly minted enterprise tech to corporate legal teams backed by IT and other stakeholders in an emergent domain is no walk in the park. I thrived under these conditions and twice set new company standards for both solution completeness and transaction size.

In 2015 the company’s average ACV (average contract value) was 40K, and the single largest one year deal was 140K. We were adding new higher value offerings that would take quite sometime to integrate into our typical sales dynamics. I latched onto these and in 2015 closed a 325K opportunity with a non-traditional client. I followed that up 18 months later with a 600K transaction with a Fortune 100 company (off course there were many other transactions between those two). This particular opportunity was a first in one more key direction, it was the first time a net new client had acquired our complete product suite, a long time company aspiration. I worked on that particular deal for 18 months.

This should provide adequate evidence to control for the ‘me’ variable. I take my craft seriously and I am considered by peers and managers to be a top 10%.

The Case

If you have worked in the Bay Area tech ecosystem for sometime you will be familiar with the herd migration phenomena that is very much the basis by which high growth tech companies expand their employee base. Point of fact the two sales leaders who decided my fate at Slack had spent multiple overlapping years at Salesforce. Back in 2011 I vividly remember the very real bodily chill I felt walking onto the sales floor at Salesforce for my onsite interview. Every single person, to a man, looked eerily alike, a veritable Mormon church service. I instantly felt like an interloper, prodding on a well established comfort zone.

At Amazon in 2013 the mostly female group (5 women, 1 man) I interviewed with were almost all forklifted from Oracle within the preceding 12 months. Commendably, a long term female sales leader from Oracle had been tapped to develop and lead the San Francisco office expansion. She went all in on women, bringing in a large cohort from Oracle. As a result, the balance was heavily weighted towards women, all white women.

I recognized some faces from our shared time at Oracle a couple of years prior. I felt our common background would be a plus but was taking nothing for granted. I always hold in the back of mind the unspoken reality of implicit bias white women in American are inculcated with regarding black men, circling around a dangerous triumvirate of feelings; fear, disgust, and objectification. You just never know what is in the mind of that person sitting across from you. So always best to be on guard.

After an entire day of positive, momentum building interviews, including a presentation I performed for the group, the last of the day was a one-on-one video conference. She showed up 10 minutes late and irritable. It didn’t go well. Maybe it was the poor video quality that rendered me more of faceless dark blob more than a relatable human being? Screens are just not ideal mediums for first impressions, particularly for black people. There is simply too much working against you. At one point I clearly remember a sneer developing on her face. It was a perfunctory 15 minutes. Right away I knew I was done. She vetoed my candidacy.

The Analysis

The really stunning thing about the Slack rejection is that my experience very much aligns with the skills required for this type of sales environment. I have just proven myself in a domain with very similar market dynamics; introducing new concepts into a nascent, undefined, fluid, multi-stakeholder operational environment. These sales environments require a very thoughtful approach to engaging, educating, and crafting solutions with buyers from a diverse set of backgrounds (IT, dev, marketing, sales etc), requiring a sales person to posses a unique combination of skills including intellectual curiosity, keen listening, and a passion for creative problem solving. The very qualities that underpin my success.

The Slack interview process culminates in an onsite presentation where the candidate is required to walk the team through a prescribed agenda that includes an example of how they would introduce Slack to their current company. I spent a significant amount of time thinking and preparing for this presentation.

The Outcome

It took me a week to develop this presentation. I would be stunned if anyone of my competing candidates went to similar lengths to develop such a well thought out presentation with accompanying visuals. I am a sales person, I know how these people think.

The point is I firmly believe had I the opportunity to meet with a more diverse set of stakeholders from different ethnic backgrounds at any one of these companies things would have been different. Someone might have answered ‘Yes!’.

The Decision

After months of research, soul searching, and some travel I came upon my purpose. I had found that precious place where my experience, skills, and passion intersected with a significant need in a place I care deeply about. Africa, home.

In March 22nd 2018 I took my final flight out of San Francisco airport as a resident of that amazing corner of the planet. Leading up to this moment I had spent the past few months working towards the decision to move back home to immerse myself in the exhilarating work of contributing to unlocking the potential of our local startup ecosystem. Silicon Savanna, as Nairobi’s ecosystem is affectionately known is approaching an inflection point and needs all the experienced talent it can get. Here my experience can be appreciated, not ignored. My passion can be embraced not feared. My skills can be acknowledged, not downplayed.

My friends, pick and choose your battles, America’s racial dysfunction is not mine. Life is too short and precious to play defense all the way.



Ecosystem Catalytic Startup Studio in Nairobi.

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