Tracy writes

Our new startup, TigerEye, is remote-first. Ten years ago while at PlanGrid, I wouldn't have believed it was possible to run a company remotely, but a worldwide lockdown showed me that a better quality of work and life can be achieved. With good communication architecture and well-defined rules of engagement, decisions can be made quickly on Zoom or a phone call [1]. There are trade-offs to remote work, but to us, the benefits outweigh the negatives.

The biggest fear of remote work is that employees won't actually work — a very real possibility. According to a recent Microsoft survey, some 85% of leaders say the shift to hybrid work means they can't tell if their workers are actually doing any work. But there are ways to derisk this. I believe that remote work is available to startups in a way that is not an option for larger companies, making it a competitive advantage in recruiting and retaining the best talent.

Startups have fewer people and can move together as a unit more effortlessly. Bigger companies can be burdened by layers of mediocre middle management, making the entire org ineffective. Mandating that employees work from the office may give leadership a feeling of control, but whether having employees actually sitting in the office increases productivity or improves company culture is something that only team members can know. In my experience, the best managers know exactly what their team is working on and how much they’re producing regardless of where they sit.

Millions of women left the workforce during the pandemic to take care of their families, and many have not yet returned due to the lack of social infrastructure for childcare or eldercare in our country. To attract talented women back into the workforce we must remove the old-school belief that good work can only be done in an expensive office. As a mother of three, I wouldn't be able to achieve what I do if I had to sit in traffic and be in an office all day.

This holds true for many of my highly skilled colleagues who also have childcare and/or eldercare responsibilities. They work from home, excel in their roles, pay taxes and can handle any life challenges that come their way. And the data backs this too — McKinsey surveyed 13,000 office workers in six countries and found that those who have confidence in their working abilities, children, and a mortgage to pay, no longer want to commute to sit at a desk and do essentially the same job. 

1. Everyone on the team is excellent at communication – It is really easy to miscommunicate when working remotely, so we look for teammates who have the ability to write and speak directly and answer questions simply. Everyone writes like they talk. We’ve all agreed to move long Slack threads to a more productive phone call.  

2. Company information is documented simply and easy to find – An important variable to effectiveness is ensuring that the whole team can find information they need quickly. Since we can’t walk over to a colleague’s desk and get answers, we make sure our Google Drive and Gitlab is organized and well-documented. It does take a Google Drive and Gitlab cop, and we put our most detail oriented and vocal person on this (CTO, founder).

3. We share core working hours and embrace time flexibility – With our global team, we have six overlapping core working hours, so we know exactly when we are available to each other everyday. Beyond those hours, we embrace time flexibility, so employees can devote their most energetic hours to their most intellectually demanding tasks and also to take care of personal matters (without taking PTO or sick days). 

4. We meet in-person and work remotely together – There is no substitute for in-person connection, so we do it at least once per month. While saving on office costs [2], we invest in travel so we can look each other in the eyes. Once a month our Dev team gets together in-person. There are also regional in-person workdays (e.g., Bay Area folks get together once a month). Every two months, our Go-to-Market team regroups in-person. We also offer WeWork passes for anyone who needs to get out of the home environment. When in-person, we make sure to eat together, because something magical happens when we break bread as a team.

5. Recurring meetings with purpose – One of our commitments to each other is speaking openly about the hard things. We can be honest, disagree, and be respectful at the same time, and we carry this commitment into all our meetings. Our weekly recurring meetings include All Hands (alignment, lessons learned, open questions and discussions), Whiteboarding (for team problem-solving), Customer Updates (covering all aspects related to prospects and customers), and Show and Tell (providing progress updates).

6. Culture of wholeheartedness (copied directly from our core values) – Life is hard even for the most fortunate of us. Building a company while living life will be challenging. The best we can do is to be wholehearted in everything we do. Be wholehearted in our personal lives. Be wholehearted when we are working. When we split our hearts into multiple pieces in multiple directions, we will get overwhelmed and be mediocre at everything.

[1] Remote work may not be feasible for professions in industries like construction or manufacturing, as their roles often have hands-on responsibilities.

[2] PlanGrid’s 2011-2019 all-in office cost revolved around 10% of total opex spend. All-in cost includes rent, utilities, insurance, tax, food, security, vending, cleaning, facilities team and more.

I often receive inquiries from female founders and execs on how to announce their pregnancy to investors and/or board directors. It appears that very little is written about how to talk about one of the biggest moments in many people’s lives. So I’ve created this FAQ in case it’s helpful to a parent.

I am fundraising right now, should I tell potential investors that I am pregnant?

I fundraised while I was eight months pregnant. This was during the COVID-19 pandemic, so most conversations were happening via phone calls and Zoom. After I got the offer, and before I signed the term sheet, I disclosed that we would be taking maternity leave in a month. The offer did not evaporate and our investor told us to take the time we needed. In general, I would not do business with someone who isn’t going to support me as a mother and human.

When did you tell your board about your pregnancy?

I was nervous to tell my board that I was pregnant. I didn’t know how they would take the news, because I am also married to my cofounder — which meant that two founder/execs/board directors would be on parental leave at the same time. 

At 21 weeks, after the second-trimester ultrasound and prenatal tests confirmed my pregnancy was viable, I told my board I was pregnant. It was also around the same time my baby belly started to show.

How did you tell your board?

I made the announcement in person at the beginning of a board meeting. Instead of calling each one individually, I found it easier to make the announcement all at once. When I told my board, they had huge smiles and looked genuinely happy for us. In hindsight, if their reaction was anything less, it would have been a red flag. But luckily we had no jerks on our board.

What did you prepare when you told your board?

The only thing I prepared was who would serve as interim CEO. I had selected my CFO to serve as our interim CEO during my upcoming leave. It is possible that your board might have a difference in opinion on who should lead as interim CEO, but it’s important for the CEO to lead the board on this decision.

What was the maternity leave arrangement you agreed to with your board?

I told the board I would take four weeks off even though our startup had a three-month parental-leave policy. I ended up needing more time to heal and went back to work at six weeks postpartum. 

For our internal team, I announced my pregnancy and parental leave schedule and shared that our CFO would be in charge. I joked that they shouldn’t burn the place down while I am away.  I also had a written maternity leave plan on Google Docs, which everyone had access to, that itemized the goals I expected each leader to see through while I was gone. Each department leader and I created these goals together to ensure we were aligned across the business.

What would you do differently?

I could have also been more creative about my ramp back into work. At my friend’s company, they had a phased-return policy that asked new mothers and fathers to come back to work one day the first week, two days the second week, three days the third week and so on until they were back to a full five-day work week. During the first three weeks back, they were not to lead any projects or try to cram a full week's work into a shorter work week.

I get asked for fundraising advice often. Here’s a cleaned up version of my answer:

1. Understand that VCs have their own investors, and their top priority is delivering a substantial return on investment to their LPs.
2. Early stage investors evaluate thousands of startups, listening to hundreds of pitches each year, but only invest in a fraction of them.
3. Investors are skilled negotiators, so avoid playing games with them.
4. The best investors can discern your intentions with remarkable accuracy, a valuable skill in their line of work. Avoid posturing or lying to yourself about your startup’s purpose and impact.
5. When you hear a “no”, move on. 
6. When you hear a “yes”, know that the deal is not done until money is in your bank account.  
7. In general, time kills all deals. So timebox fundraising and stick to it emotionally and practically. Return to building and talking to users even if you haven't secured a term sheet after the predetermined period.
8. Fundraising is just a financing event; don't become infatuated with it or let it lead you into a state of depression.
9. Fundraising is not an indication of success or failure, it is an indication that you now own less of your company.  
10. If you’re not in 100% fundraising mode, don’t talk to VCs (unless they're good friends or family).

This article previously ran in TechCrunch+

I previously served as the CEO board director at PlanGrid, and as an independent board director for two startups. I believed in the leadership and products at those companies, but I resigned from both startup boards because I couldn’t bear sitting through another company’s board meeting. I wrote an article in TechCrunch+ to offer advice on how to run an effective board meeting.

Time is a fixed resource. As a board director, it's crucial to be helpful to the leadership team with the limited time we have. Otherwise, attending board meetings becomes pointless. Concise materials can make board meetings more effective and leave room for useful conversations.

After Initialized and Next47 co-led TigerEye’s Series A, and a formal board of directors was put in place, this is what my cofounder and I wrote to them:

Dear Board,

From the start at TigerEye, we promised ourselves we would use our experience to our advantage by making better decisions across all vectors everyday. “What did we do that we never want to do again?” One thing we’d like to never do is the three-hour, too-in-the-weeds, non-strategic board meeting. Here is a memo we wrote instead of preparing a board deck. We hope this memo gives you the punchline on the business and how we’re thinking about the future, allowing the majority of our time together for meaningful conversations.

With gratitude,

Tracy & Ralph

We discuss what we accomplished in the last three months as a team and what we’re doing in the next three. Then it's an open discussion where we push ourselves to have the hard discussions on worst-case scenarios and how to de-risk against them. These conversations typically revolve around the competitive market landscape, our direction as a company, current economic conditions and a realistic check-in on how much money we’re burning and our ability to execute. 

• Eliminate 80-plus-page board decks: Every board deck I’ve made and seen is more than 80 pages long. I am not exaggerating. The challenge with this much content is there is a finite amount of minutes of attention we get from the board, and only so much information can be absorbed in one sitting. If there is truly that much material and information that needs to be communicated, consider sending out regular email updates, or having one-on-ones with the board, to keep them updated outside of the board meeting. The goal of the board materials is to quickly get your board up to speed on your assessment of the business, shine a light on the problems and get their help strategically.  
  

• Show where the business hurts the most: It is important to celebrate the hard work of the team. But I’ve seen many board decks that over-index on wins and don’t focus enough on the losses. In my experience, everytime I ignored where it hurt in the business, it cost me triple the amount of time, because problems tend to compound — and do not go away on their own.   
  

• Never bury bad news: I once experienced a situation where, with fifteen minutes remaining in a board meeting, the founders told us something that would completely change the business and put it at risk. We needed at least an hour to talk through our options, but everyone was out of time and steam at that point.
  

• Eliminate the showboat: As a CEO who wanted to give each department head autonomy, I would structure the board decks with open spaces for each executive to provide updates. The challenge with that approach is that we ended up with an incohesive, showboaty board deck where each department leader used their allotted slides to brag about their teams’ wins and defend their roles. Instead, bring your board on your journey of wins. If a big deal closes, text your board or email them as it happens. Have a good cadence of communications with the board so they feel included. This will also help to cut down on the victory lap sections in the board materials.
  

• Use existing artifacts: At my last company, it would take a few weeks to generate new graphs and artifacts for the board decks, and I’d later present them in All Hands. I now realize this was wrong. If we do our jobs as leaders, the whole company already knows how we think of our business and understands near- and long-term goals and how we are working hard at pushing the company forward together. A good way to capture and communicate the direction of the company is to have the team create artifacts that highlight the business, so they’re brought along early — and present those materials to the board.
  

• Allow for closed-door sessions: A valuable lesson I learned from being on a board is the importance of closed-door sessions. The CEO held a beginning closed-door session to go over legal matters without their executive team. Then, there were two closed sessions at the end, one with the CEO and board and one with only the independent and investor directors. This gave the board space to debrief, discuss how to be most helpful, and create an action plan. One of the directors would then follow up with the CEO. Closed-door sessions allow for open and honest communication and can lead to more effective decision-making. 

The responsibilities of a board at a startup can vary depending on the size and stage of the company, but generally, the board is responsible for overseeing the company's management and ensuring the company is run in the best interests of its stakeholders (shareholders, employees, customers and the wider community). Keep board decks short so all parties can focus conversations on the long-term sustainability and success of your company, which includes managing finances effectively.  By doing so, the board can contribute significantly to the growth and success of the startup.

I had the privilege of leading PlanGrid to $100M in ARR before I stepped down as CEO and passed the baton to Autodesk Construction. I’ve had years to dissect the mistakes I have made in my first startup, and I’ve now taken my lessons learned to TigerEye.

Our failure points: 

As first-time founders we were too creative about organizational structure. We had a flat management hierarchy in the early years, and we bragged that we ran our startup like Star Trek — you were either in engineering or operations, and everyone reported to a founder. This was cute, until it quickly stopped working. People care about titles and career paths, and if you want to retain great people, you have to care about these things too. 

Takeaways: Be creative on how you’re solving problems for your customer — don’t be creative about org structures. Hire a great HR leader as a business partner to help recruit and retain the right team, and architect a good communication flow. And remember that A players can recruit other A players, but B players usually end up recruiting C players.

Our trickiest inflection point was hitting Dunbar’s number — at 150 people, everything went to chaos. Hierarchy is a factor. At 10, 20, or 30 people, everyone can report into a founder — at 150, just based on basic management ratios, there's now three to four degrees from the frontline team member to the founders.  

Another heartbreaking side effect with growth is that the people who helped get the company to its current success may not be the right people to grow it the next five years. 

#3: An executive not working out

My biggest mistake was hiring a big-public-company tech executive with a fancy resume who had never worked at a startup. And although everything in my gut told me that they were the wrong fit, I felt so underwater with work that I convinced myself that my life would suck less if they were just in the building. 

As we grew to nearly 500 people, we would have several versions of the executive bench. The best indicator of an executive’s success is that they have already done the thing you want them to do at exactly the same stage that you are in and want to grow to. With that said, I do believe a first-time executive with raw talent and a growth mindset can be successful. In my case, at my first startup, it felt risky to be learning on the job as a CEO and be surrounded by other leaders who were learning on the job as well. Luckily it worked out for us. 

Here is a brief list of red flags on an executive who isn’t working out:

1. They frequently use the wrong pronoun “I” followed by “[contribution to the company]”.
2. You dread having 1-1s with them.
3. They blame you or their peers.
4. They complain laterally and downwards.

#4: Losing product market fit

Construction people used our software because they loved us.  If construction folks were using our competitors' software it was because they were told to. In enterprise software, the best product doesn’t necessarily win, and there is a long trail of great enterprise software under tombstones.

Selling to the enterprise requires a series of features and products that have nothing to do with making the end-user happy. There is security red tape that the non-user buyer cares about: RBAC, SOC2 Type 2, ISO270002, Admin Consoles, SSO and more.

Prior to PlanGrid’s acquisition, in my last years of leading the company, our growth slowed to high double percentage year-over-year growth while our competitor’s growth was rumored to be triple digits. We needed additional growth levers. We pushed towards internationalizing our product. We launched two new product lines with small scrum teams and slim budgets. Concurrently, we were knee-deep in technical debt and our Vice President of Engineering quit with no notice. These were rough years. But through hard work and great people who continued to pour their heart and soul into the company and customers, we hit almost all our milestones and secured the attention of Autodesk, our future acquirer. 

#5: Life happens

I’ve come to believe that a big part of our jobs as founders is to manage our own emotions. It doesn’t matter how well we were doing; it never got easier. Life doesn’t stop just because we’re doing the hardest thing we’ve ever done before.

I remember how excited we were to get accepted into YC’s Winter 2012 batch. As we were launching our product into the world, living the entrepreneurial dream and sleeping and working out of our Silicon Valley hacker house, we were also experiencing the cruelness of life. In between demos and code commits, we greeted hospice care at our doorsteps. We watched our cofounder battle, and ultimately succumb, to cancer at age 29.

Takeaways: Life is short and hard even for the most fortunate of us. And that’s why, whatever you have chosen to work on, it has to be worthy of your time here. Because if you have any success at all, it will take up at least a decade of your life. And if you’re really lucky, you get to work on it for multiple decades.