You got the startup job offer! Now what?

You got the startup job offer! Now what?

I’ve been working in the startup ecosystem for the last decade, both as an investor and operator. As a result, I am often asked for advice about finding the right startup to join and then negotiating a startup job offer. Here is a consolidated set of my advice, tips, and resources for people wondering how and what they should negotiate for in their job offer.

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UltiKro: A match made in heaven or excel?

UltiKro: A match made in heaven or excel?

HR software is big business. Big business means big mergers. Kronos, 43-year old maker of on-premise workforce management (WFM) software navigating a transition to the cloud, and Ultimate Software, cloud-based human capital management software (HCM) provider for mostly mid-market customers, agreed to merge in a blockbuster deal. It's worth noting that private equity firm Hellman & Friedman owned both companies, having bought Kronos in 2007 and Ultimate in 2019. That this transaction would take place was a mostly a foregone conclusion. Now that it's been announced, there are some significant implications for customers, and the HCM/WFM space more broadly. Does the combined entity have more to lose than to gain?

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NRF 2020: Experience, experience, experience

NRF 2020: Experience, experience, experience

This week I attended NRF, Retail's Big Show, for the first time. The sheer size of the production is nothing short of impressive. Navigating the 840,000 square feet of the Javits Center in New York, it's hard to believe retail is struggling through a 'retail apocalypse.' The show is a beacon of retail strength, with a reported 40,000 attendees representing retailers, vendors, consultants, media, and thinkfluencers from across the retail spectrum, walking the conference in search of their place in the future of a $30 trillion industry. Three major themes emerged from the show, all centered around better experiences.

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My Next Chapter

My Next Chapter

2019 was a year of new adventures. I transitioned into an advisory role at Poynt, where I had spent the past five years helping over 100,000 businesses get access to technology to supercharge their business growth. I navigated the early days of learning how to be “Dad” after welcoming my son into the world in late 2018. I had the opportunity to work with some incredible early-stage founders as an angel investor. Now, as a new decade begins so does my next chapter: Legion.

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fiserData: A behemoth is born, but is it enough?

fiserData: A behemoth is born, but is it enough?

A financial powerhouse was born as Fiserv agreed to buy First Data for $22 billion in an all stock deal. The news comes as a surprise for many in an industry that doesn’t see transactions of this size very often. The combined company (which will go by Fiserv in a tragic waste of an opportunity to rebrand) forges a mammoth technology vendor attempting to prove that despite all the noise around young tech companies like Square and Stripe, old dogs can also learn new tricks. The big question is whether it is too little too late.

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Your startup is not your baby

Your startup is not your baby

Building a startup is an entirely different experience from raising a child. There isn’t a pre-seed or seed round for the baby to help get you off the ground, despite the fact the product has been built already and there are over 7 billion examples of product-market fit. Yes, you can hire people to help care for the baby but you’re not going to be able to bring on hundreds (or thousands) of talented, capable and experienced people, aligned on the mission and vision, working together with a shared sense of purpose, to help take care of the infant. Incidents in the middle of the night are always a shitshow, and there isn’t a diaper-ops team in India around to take care of it. On top of daily stand-ups there are lie-downs, tummy time and crawl arounds. One on ones are impromptu, with unclear agendas. Conversations are one sided instead of collaborative, and most of the time you wonder if the other side understands what you’re saying in the first place. And bored meetings are more mind-numbing than you’d expect.

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