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Meet the Startup That’s Keeping Workforces Connected during COVID, as Revealed by Sean Jackson of Sift

kokou adzo



Sean Jackson Sift

First of all, how are you and your family doing in these COVID-19 times?

Sean Jackson: 2020 has been a rough year! My partner and I are both career-driven, and as such, we’re working well more than the full time when the pandemic dawned. The switch to work from home came bundled with figuring out new child-care solutions for our 3-year-old daughter. The first 4 months were really rough. My partner and I switched from being professionals one minute to helping our daughter put a bandaid on an (often mythical) wound from some household exploration done with less than ideal paternal support. We’ve since joined with a few other professional families and are doing a sort of nanny-share combined with village child-rearing where we all rotate shifts of watching a gaggle of kids from ages 2 to 4. The silver lining is much more time with my daughter, and it’s been incredible to watch her learn her letters and grow! 

Like many places in the country, here in Michigan, the nursing home populations have been hit especially hard. My father suffered a stroke three years ago and, due to a loss of mobility and cognitive function, lives in an assisted living facility. It’s been really challenging for the safety of residents, and I have not been able to visit with him in person since March. I do video calls with him, but he does not quite understand what is going on due to the stroke’s side-effects. It’s frustrating and nearly breaks my heart each time we have a call but can’t quite communicate, but I’m grateful that he’s been healthy despite a number of COVID cases in his facility.

Overall, I’m fortunate. While my family has experienced hardships and furloughs, we have our health and have been able to keep our heads above water. Many are not as fortunate as we’ve been. Where we can, we’ve been giving back to our community through donations to local food banks and volunteering with local cultural outreach programs. Everyone is going through a hard battle right now.

Tell us about you, your career, how you founded Sift.

Sean Jackson: I’ve held roles in a range of industries: I started my career in the Marine Corps working on disaster response in places like Haiti and the Philippines, and economic development in Afghanistan. I then moved into policy while working on Detroit’s bankruptcy, followed by the private sector for a large conglomerate in Detroit. Regardless of the organization’s structure or goals, a constant thread was that there were experts in nearly any challenge you might face. However, despite having thousands of ‘colleagues,’ in practice, you only knew the 10 to 15 people you worked closest with: leveraging the skills or experience of anyone outside of your personal professional network relied on the tribal knowledge of others, and a good deal of luck.

The magnitude of this problem struck me as I was reaching out to an old college friend on Facebook to get a perspective on a challenge I was facing at work. It struck me as insane to be reaching out to someone I hadn’t talked to in half a decade as the ‘closest’ person I could find, when there must be dozens of people inside my own organization who had answers and perspectives that were much more relevant. I just had no way of knowing who they were or how to get in touch with them. We have so much access to our personal networks via consumer tools, but the people we work with for the majority of each day are inaccessible and distant by comparison.

We founded Sift to help organizations leverage the immense power of their internal talent networks and make organizations more human in the process. We feel it should be easy to understand your peers’ knowledge, skills, and experience across your organization and understand your colleagues as more than just titles on an org chart.

How does Sift innovate?

Sean Jackson: The world has changed a lot since the mid-1990s: the internet is now ubiquitous, with magic computer rectangles in our pocket, and the rate of change has never been faster. However, if you were to look at the set of tools someone on the cast of Friends would use to manage the show, it would look basically the same as today – email, Word Processor, Excel. The tools an office worker uses today are an evolution of the tools they worked with back at the turn of the century, despite the fact that the way we work is radically different.

We’re introducing an entirely new category of tool (a people search engine) into the mix. We’re basically telling enterprise organizations to make a small but fundamental change to the way their people work. You’re freeing your people to cross chains of command, trusting them to leverage the right colleague when they need them, and basically saying “work however you want if it helps you achieve our goals.” For some organizations, this is just a tool that enables their collaborative culture, letting them realize a vision that they’ve held but never been able to achieve. For others, this is a big culture shock.

We’re betting that the world is trending towards more transparency and collaboration, and our ideal clients are some of the world’s largest companies. Helping forge that changes to better align with a new paradigm is not always easy, but we continue to innovate by consistently being problem-focused rather than solution-focused. The problem that we’re focused on is understanding how to help organizations leverage their most valuable resource – their people. The way that we first approach solving this problem is rarely the right answer, but if you have a meaningful problem, you can have a massive impact when you finally figure out the right solution. We take this approach not only in how we build our product but also in how we work as a team. We welcome ideas no matter who it comes from, we challenge our assumptions, and we’re always testing new hypotheses. We’re constantly in a learning mindset as a team, and that’s the secret sauce to how we stay innovative.

How the coronavirus pandemic affects your business, and how are you coping?

Sean Jackson: As with many businesses, COVID-19 has greatly affected the way our team works together. We’re a small team that’s used to working in the same space. We’re used to turning to each other when we have questions or want to collaborate quickly on something via whiteboard scribbling. Now, that’s not possible, and we’re stuck behind screens plus a few communication channels in order to work together. We’ve found that although we’re communicating just as much, and maybe even more often, information slips through the cracks. You would overhear in conversation at the office, or problem-solve/brainstorm spontaneously in-person gets stuck in a Slack channel or DM. We’ve adapted in a few ways. Whether it’s altering our all-team standups to increase visibility across our teams to holding team hangouts/game times a few times a week, we’re working to stay connected, stay communicating, and ultimately stay collaborating. 

In terms of how the pandemic has affected our business as a whole, the employee experience has now become the digital experience with the move to remote work, not only for Sift but for all companies. That has actually created an opportunity for us in that companies are looking for tools that enable people to find, discover, and connect with one another. Before 2020, digital transformation was a buzzword, but when COVID hit, everyone was pushed to move faster. Now that we’ve been working remotely for months now, organizations that rushed to get even the most basic tools in place are now looking to fill the gaps in their employee experience. At Sift, we’re obsessed with understanding how great employee experiences come to life. We use those lessons to help teams create a foundation of collaboration and humanity to ultimately create a better digital workplace. Remote work is our long-term, and we’re helping businesses prepare for that long-run.

Did you have to make difficult choices, and what are the lessons learned?

Sean Jackson: We’ve been lucky in that from a team member perspective, we’ve been unimpacted. We closed our Series A right as the pandemic dawned, and as a SaaS company, the transition to remote was jarring, but we took it more or less in stride.

Perhaps the biggest challenge we’ve been facing is how to learn from the market and customers when many of the traditional sources of getting yourself out there – conferences and events – are closed or virtual. Last year I spent a good part of the summer and fall on the road at conferences, and insights gained from conversations there really drove our roadmap and pipeline. Thus far, we haven’t found a real replacement for the spontaneous conversations you have walking out of a talk or on the expo floor of a conference.

How do you deal with stress and anxiety? How do you project yourself and Sift in the future?

Sean Jackson: It’s a struggle. As an individual, it can feel like the entire world is on fire: work, kid, relationship, parents, and friends. While I sometimes feel underwater, I try to focus on the old saying, “all you can choose is your reaction.”

To me, this means both having an active plan for what I’m going to do each day and week and accepting that that plan will probably not last long when faced with reality. The process of planning and (attempting) to calendarize my week helps me align on what is really important to get done, from a work, household, and relationships perspective. By putting something on my calendar, I’ve affirmed its importance, even if I end up having to move it. It keeps me from dealing with the tyranny of the recent.

I’ve tried to take this strategy beyond myself, and to our team, we each set ‘promises’ for the week and actively share them with each other each Monday. Each week we also look back at the past week to see how well we lived up to our promises. Stuff happens (the lesson of 2020 if there is one), but in general, we want to accomplish the things we set out to do, and try to have some control over our time (as much as one can).

I also believe in having things to take your mind off work (and dare I say it, family, too). We are all our own humans and need space that is just for ourselves. For me, this has been running (I run for 20 miles a week) and working on restoring a beat-up old Miata in my garage. Running both gets my blood flowing and gets me outside while working on the Miata forces me to learn about something I am a complete novice at and work with my hands (not something you do much working remotely in SaaS!)

Who are your competitors? And how do you plan to stay in the game?

Sean Jackson: Pingboard out of Austin, Texas, and Structural in St Louis are our closest peer competitors, though we aim for the enterprise end of the client spectrum while Pingboard and Structural aim towards SMB and mid-market.

Though honestly, the big “competitor” for all of us is those who just don’t have a current solution for understanding the knowledge, skills, and experience of their workforces. In most organizations today, this is either serviced through tribal knowledge or home-brewed employee directories with limited information beyond name and job titles.

 For us, “staying in the game” looks like staying problem-focused rather than solution-focused. Constantly questioning and learning about the problem we’re to solve, the challenges that companies and individuals face, and how we can speak to some of those pain points. The rapid switch to remote work has exposed a lot of pain in terms of collaboration inside the enterprise: who is working on what? Who can help me solve this problem? Who is the new team member who just started in marketing, and what do they bring to the table? 

We’re focused on understanding the challenges related to keeping teams collaborative as organizations become more virtual, and building comprehensive solutions that integrate into other existing ecosystems of tools organizations leverage to get things done.

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Kokou Adzo is the editor and author of He is passionate about business and tech, and brings you the latest Startup news and information. He graduated from university of Siena (Italy) and Rennes (France) in Communications and Political Science with a Master's Degree. He manages the editorial operations at

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