Founders Spotlight — ChartHop

CoFound Partners
8 min readOct 8, 2020

We are excited to launch our Founders Spotlight series, starting with ChartHop! After joining the early beta in May 2019, we invested in their Seed round led by Andreessen Horowitz.

We sat down with Ian White, founder, CEO and CTO of ChartHop who recently announced its Series A led by Andreessen Horowitz (a16z). Prior to ChartHop, Ian was the founder and CTO of Sailthru and before that, he was the first head of engineering at Business Insider.

Through these experiences, Ian felt the pains of manual people planning and building teams. He founded ChartHop to address the strategic needs of people leaders so they can plan with alignment and context.

ChartHop is the world’s first organizational management platform, empowering leaders and team members alike to see the past and present of their organization and design its future. The platform automatically builds fluid, data-driven views of a company through real-time updated org charts, custom reporting, and headcount planning tools that boost efficiency and transparency across teams. Simply put — ChartHop makes organizations run and scale better.

Since its launch in February, ChartHop has been rapidly growing. Companies like BetterCloud, Lightspeed, Starburst, and InVision rely on the platform, and over 40 founders and c-level executives have personally invested in the company.

How is it starting a company the second time around? Has it been easier?

For the most part, it’s a little bit easier the second time around. You always try to learn from both successes and failures — I think it’s good to have some of each!

The biggest difference is, I can see the road ahead a little bit and have a pretty good picture of what the company will look like a couple of years from now — and try to plan for scale ahead of time. At ChartHop we’ve started very intentionally with clarity of org structure — roles clearly defined, levels and bands from day one, everyone looking at the same KPIs. A lot of startups put this work off for later, and it comes back to bite them.

The biggest change of mindset is understanding that it’s a marathon, not a sprint. You have to move with energy and purpose, but really build for the long haul and pay attention to not let anyone burn out. Because of this, even though we are growing and moving rapidly, we’ve instituted FlexFridays. FlexFridays allows employees to take off every other Friday either to take care of their kids, to catch up on email/other work, or simply to reset and take their mind off of work.

Tell us about how you started ChartHop and how you went from MVP to term sheet.

When I was building my last company, Sailthru, we had good software tools for every aspect of the business — except the people side. For some reason, people software is a backwater and everybody resorts to spreadsheets for anything serious. I knew there could be something better, so I spent two years building the software I wish I’d had.

The bar for any new SaaS company today is high, so I wanted to have a very robust, and tested, product before fundraising.

After I left Sailthru, I consulted with a number of organizations, big and small. I saw the same org management issues pop up again and again. The challenges we faced at Sailthru weren’t unique — they’re actually quite prevalent for every operating leader.

I knew that to build an ambitious business, we would need external capital. However, the bar for any new SaaS company today is high, so I wanted to have a very robust, and tested, product before fundraising.

Once I felt the product was ready, I was introduced to David Ulevitch, general partner at Andreessen Horowitz (a16z), and I demoed the product. The meeting was pretty casual — I didn’t have a pitch deck, I just shared the product and the vision. But, as a former operator, he immediately understood the need and potential for our solution.

This ultimately led to a16z leading our seed round. To make things even more exciting, my son was born right around the same time. It was a hectic time to be sure, but I couldn’t be happier with where we are today.

The explosion of HR Tech over the years has created many data silos. Getting accurate, real-time data about personnel is tedious and error-prone. How are you guys thinking about ChartHop’s position and role in the broader HRIS ecosystem?

People data is incredibly important for the day-to-day management and for making strategic decisions.

People software usually hasn’t focused on strategic data-driven insights.

The first wave of HR Tech was really about automating processes and housing data rather than building bridges between data. The past few years have given rise to many verticalized solutions for HR that have then created gaps and inconsistencies across systems.

These tools have helped HR move beyond paper but they still rely on spreadsheets to do any of the strategic work. On top of that, none of these tools have ever been built for operational leaders — and people data is incredibly important for the day-to-day management and for making strategic decisions.

So that’s what we’re here to change.

How has it been starting ChartHop as a solo, technical founder? There are so many schools of thought out there but I’m curious to hear your experience.

Building a great product is the most important part of starting a company but as a founder, you have to be able to sell — sell your vision to potential team members, sell the product to potential customers, sell the opportunity to potential investors.

As a technical founder, the biggest advantage is that you can build whatever you want. You can build something almost as quickly as you can imagine it.

However, this can also be a double-edged sword. Building a great product is the most important part of starting a company but as a founder, you have to be able to sell — sell your vision to potential team members, sell the product to potential customers, sell the opportunity to potential investors.

Because I am a second-time founder, I know the importance of moving past the phase of building everything myself and the need to empower a great engineering team to build without depending on me. That’s why my first couple of hires were senior engineers.

I’m both CEO and CTO at ChartHop, and I’ve found that success in these jobs requires, above all, great communication. Just because you build it, doesn’t mean they will come.

Success comes from both building something great and communicating the value of it to the market.

It feels like ChartHop has created a new category for people planning software which is remarkable given how crowded HR SaaS has become. Narrative matters a lot so I’m curious to hear how you’ve positioned your GTM and lessons learned on product marketing.

The HR SaaS space is very crowded right now, but current offerings are primarily vertical solutions. They handle operations and tactics for specific areas of a company, but don’t help leaders build a cohesive strategy across an organization. ChartHop provides that single point of access that has been missing from HR software for far too long. HR leaders feel this pain — and as soon as they see the product their eyes light up with the possibilities.

Managers need access to information to make the right decisions for the employees they manage.

From a target market perspective, HR software has traditionally been marketed solely to HR leaders.

But why should that be the case?

Managers need access to information to make the right decisions for the employees they manage. Our software is built to empower everyone across an organization. By providing value for the leaders across the organization, we’re able to save HR time while also using any functional leader as an entry point.

How have you assembled your founding team? Any helpful stories around courting and recruiting you can share with us?

I believe a company’s most important asset is its people.

And as CEO, one of my favorite parts of the entrepreneurial journey is building great teams. That requires a balance between hiring from a network of trusted professionals and expanding your search to include a diverse set of individuals who can bring new perspectives and experiences to the table.

There’s been a fun element of “getting the band back together” — around half of the early team are people who I worked with previously either at Sailthru or Business Insider. In some cases, I hadn’t worked with people in several years and it’s been great to reunite on a new challenge.

An image of ChartHop’s Org Chart highlighted by whether they’ve worked with Ian before.

Building a team is all about assembling a group that can complement your core strengths and weaknesses.

We’re building a product for everyone and so I tried not to just hire people similar to myself. As a result, women make up more than half of our leadership team and 67% identify as part of a historically underrepresented group.

What’s next for ChartHop? With this new round of financing, what are your priorities and how are thinking about your role evolving in this new growth stage?

With this latest round of funding, we’ll remain focused on growth for our product and team. I still spend a lot of time working on the product so we’re excited to hire a bigger engineering team that will enable me to spend more time on the GTM and strategy side.

One new product we’re very excited about is our Diversity, Equity, and Inclusion (DE&I) reporting offering. We’ve found that while organizations track employee data, so many lack the necessary structures in place to keep diversity information updated in a way that would help them make meaningful changes.

This feature is offered as part of ChartHop Build, our base package, because we believe DE&I initiatives should be an integral part of planning from day one and not something companies audit once a year. Pairing this with our new compensation planning module means that we’ll be able to give companies the tools they need to ensure proposed compensation changes are equitable before they actually go into effect — decreasing the retroactive fixes companies have needed to make after external audits find inequitable compensation practices.

Sample report comparing today against the proposed scenario. This way, managers can immediately see how the changes they’re proposing perpetuate (or fix!) pay gaps across races before they go into effect.

What advice would you give founders who are starting businesses today?

  1. Don’t just start something to start something. Entrepreneurship has developed a very sexy aura around it and the blood, sweat, and tears it takes to build something are often overlooked. Above all, work on a problem that you find personally interesting because you are committing (hopefully!) at least ten years of your life to it.
  2. The market has high expectations. Work with a group of early beta customers to get real feedback and get to product/market fit before raising a real round.
  3. Build your team and design the org you want from day one. Make roles and responsibilities hyper-clear — KPIs and OKRs are great ways to do this. Share this information across the organization, no matter how small, so you can ensure alignment throughout.

CoFound Partners is an early-stage venture firm helping founders build a repeatable sales motion.

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CoFound Partners

CoFound is an early stage venture firm helping founders build a repeatable sales motion.