Operator Spotlight: Lucid Co-founder and CEO Karl Sun

Looking for practical help and advice on an operational area that may be outside your realm? Each month we spotlight one of our talented operators, who’ll share their expertise and offer insights and ideas that may help improve your own operations. This month we spoke with Karl Sun, co-founder and CEO of Lucid Software.

Your company has been on quite a ride over the last 10+ years and just tripled its valuation. Describe what Lucid does and the problem it’s solving. 

KARL: The Lucid business is built on our foundational mission to help teams see and build the future. As we see it, there is a massive shift happening in the way that teams work together to build new products, new processes, or new strategies. These activities require that teams be able to work side-by-side to understand how their business works, and how to make it better.

We provide a unique approach to collaboration. Instead of relying on endless text to get a point across, our applications allow teams to work together on a shared canvas from anywhere in the world. Many have turned to our products, Lucidspark and Lucidchart, to bring their teams together virtually, and in so doing have discovered that this new way of working and collaborating is even better than what they were doing before. 

COVID has forced us all to rethink workplace collaboration and given rise to new ways of working. As a visual collaboration suite, how does Lucid fuel the future of work, while avoiding the trap of zoom/slack fatigue?   

KARL: Sometimes communication and collaboration are talked about synonymously. But the truth is many companies are acquiring tools that optimize for communication and hope that those solve their collaboration problems. In the context of a hybrid workforce, the power of a common visual language breaks down physical and digital communication barriers so teams get the big picture, achieve a shared understanding and align on next steps. The Lucid visual collaboration suite gives teams the chance to work side-by-side, no matter where they are located.

Right before Lucid, you were at Google for several years. What was the biggest mindset shift you had to make going from a $23 billion company to starting from scratch as a team of two?  

KARL: I actually came on initially as the first investor, but then my co-founder Ben (who was still in school at the time) eventually coaxed me into joining full-time. We worked out of a student apartment for a while — it couldn’t have been more different than what I had just left at Google. With a brand like Google, we could get any meeting with anyone. Starting from scratch with an unknown brand, we had to be a lot more scrappy to get any kind of attention. The product really had to speak for itself, so we spent most of those initial years making sure it was so good that people couldn’t ignore us. 

Another thing is, in a smaller company, you have to focus on the most essential projects that produce results and lead to progress. There’s an incredible need for everyone on your little team to be accountable and have a drive to do their best on every single project. 

Lucid had wild success with its freemium product before moving towards B2B SaaS. What advice would you give to other founders following that path? 

KARL: As we thought about growth, particularly before we had a sales team, we focused on three things. 

  1. End user outreach: We put a lot of effort into making sure that current and potential users understand we can solve a need that they have. This involves a few things, but one of the biggest factors is our focus on SEO. We rank for over 1000 keywords and phrases.
  2. Joining ecosystems: One of the main tenets of our products is that users can use Lucidspark and Lucidchart in the systems where they work. To enable this, in the beginning we worked really hard on our integrations and being available in different ecosystems. Having Lucidchart included in the launch of the Google Chrome Web Store and Google Apps Marketplace and being able to grow up in the Google ecosystem was huge for us early on. But now you can also find and use our products within Atlassian’s ecosystem, Microsoft 365, and Slack, to name a few. 
  3. Sharing and collaboration: Because of our focus on collaboration, we also see a lot of users come in through their exposure to a diagram or board that someone else has created and shared with them. Better collaboration not only makes for a better experience for the user, but it also then becomes something that they want to share with others to solve their same pains. This exposes more and more people to our products.

If products are conducive to these three things, there’s a lot of potential for going the freemium route.

There are many ways for CEOs to evaluate business success in a SaaS context. What are the most vital company-level metrics that you personally rely on?

KARL: In the early days, it was definitely user numbers. The main goal was to get more and more people into the product and just increase our general product awareness. More users in the product also meant we were able to collect more feedback to help make things better. As we started to mature beyond that, we started to focus more on usage and conversion rates. Those metrics helped us know we were making a product that was compelling enough that people were paying for it. 

Now, we’re focused on successful users. There are a lot of factors that we evaluate to determine whether a user is successful or not, such as how much time they spend in the product, whether they get to an outcome, etc. 

You’ve shared great insights on the people side of entrepreneurship. What have you done to maintain lasting connections with employees in today’s virtual world? 

KARL: Our company was office-based prior to the pandemic, so the shift to remote work was new to us and we really did have to rethink how we made sure employees still felt connected, especially to our leadership team. So we made it a goal to over-communicate as much as possible and bring our employees along with us as we made decisions. 

We increased the frequency of our company-wide emails and all-hands meetings. We also added a slack channel to these meetings to promote interaction and connection across the company as we adjusted to our new way of working. 

We tried to transition as many of our engagement activities to a virtual setting as possible. For example, we have an internal talk show called The Oatmeal that two of our employees started as a way to learn more about employees across the company on a personal level. We utilized that platform to help employees engage with leadership by interviewing a new executive team member each episode. This type of interaction is really foundational when building lasting connections between leaders and their teams. 

In your opinion, what are some ways the tech and venture industries could do a better job of empowering the next generation of diverse leaders?

KARL: Even though we have a lot of work to do with diversity in general in the industry, there is usually even more of a diversity problem in leadership positions compared to entry-level roles. So, I believe it’s really important to actively identify those diverse employees who are earlier in their careers, and are top performers or have high potential, and actively mentor them to be leaders in your organization.

AOC often talks about the skills she picked up as a bartender, and others talk about what they learned working retail. What were some of those formative jobs for you?

KARL: I learned important lessons from my first three jobs. 

My first job was reclaiming usable old bricks from demolition piles and stacking them on pallets. This taught me that sometimes the work isn’t fun, but it still needs to get done. It also taught me the benefits of a desk job and gave me an appreciation for air conditioning. My second job was bagging groceries at the supermarket. This gave me experience in direct customer service, and was also where I learned the importance of mastering every job, no matter how small. 

My third job was working at a summer camp for teenagers and my favorite part about that job was being exposed to so many different kids and counselors who had such unique interests and talents, and watching them come together to create some pretty amazing things. It gave me exposure at a formidable time in my life to the good that can be done when people with diverse backgrounds, perspectives, and experiences come together.

What’s your secret super power? 

KARL: I think I’m a good judge of talent. Part of that is identifying people who aren’t obvious fits (seeing beyond work history or experience) but have something in their background to suggest they have high potential. I also believe in looking at a group as a whole and understanding what needs to be added to the mix, whether that’s skills or personalities, to really complement the group and help the entire team be successful. 

The flip side of that is I also think I have a good BS detector 🙂

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or on Twitter and LinkedIn.

Our virtuous cycle: when operators do venture

I had ulterior motives for starting Operator Collective back in 2018. 

Sure, the core idea was always to bring together as limited partners (LPs) active operators from diverse backgrounds who had built the world’s most admired companies. They have the very expertise founders need as they grow and scale their companies, and the most relevant contacts with both potential customers and future employees.

They also bring their operating talent and outsider perspectives to shake up the venture world. After all, what operators do best when they see a problem is come up with a solution, and then execute the hell out of it.

Even though these incredibly talented executives are critical to the success of startups, they have largely been left out of the venture world. Traditional venture is rigid, competitive, and not team-oriented. It’s just not friendly nor particularly appealing to operators—especially in the case of our Operator LPs, 90% of whom are women and 40% people of color. The doors to venture have long been inaccessible to people from underrepresented groups.

Leyla Seka has always called herself an accidental venture capitalist. She first joined Operator Collective as a founding LP while still an EVP at Salesforce. She famously built and scaled the AppExchange, launching thousands of startups along the way, and was the first to champion equal pay, setting off the wave across the tech industry and beyond. After leaving Salesforce, Leyla was considering CEO positions as her next move. When I asked whether she’d be open to help build Operator Collective, I’m grateful she agreed to come on board.

Operator Collective was created, among other things, to serve as an anchor for active operators at the top of their game to engage in venture in a way that is collaborative and flexible, with aligned incentives. A place where they could not only continue to operate or ponder their next career move, but contribute to what we’re building, deepen their investing acumen, and have a supportive community of operators. Oh and have fun along the way.

Enter the virtuous cycle. I share with mixed emotions that Leyla is returning to a full-time operating position as COO of Ironclad.

She’s also transitioning to a new Operator Collective role as Chair of our Board of Advisors. Leyla joins Erica Ruliffson Schultz, Stacy Brown-Philpot, Claire Hughes Johnson, Tekedra Mawakana, and our newest Board member, Elena Gomez (welcome Elena!). I’m thrilled Leyla will remain a close part of the Operator Collective community, leading this group as they advise me, Operator Collective, and our portfolio founders.

Our model was designed to include active, current operators. Operator Collective and the venture world are better off today because Leyla Seka brought her operator lens to all that she learned about venture, and then ran with that knowledge to create a better ecosystem. Her substantial understanding of the enterprise software world helped Operator Collective make better investing decisions, and she leveraged her years of experience advising AppExchange startups to support our portfolio founders on how to scale.

One of these companies, of course, is Ironclad, which has built an extraordinary and beloved digital contracting platform. Working closely together for almost three years, Leyla and CEO Jason Boehmig very quickly developed a special bond, and it became apparent that she was uniquely situated to vault Ironclad forward in a way no one else could. Closing the loop on our virtuous cycle, Leyla is returning to her operator roots as Ironclad’s COO.

She has already made a huge impact on the industry, and she’s just getting started. Her relationships, outsider’s view, and execution also led her to create a long-lasting and game-changing institution called the Black Venture Institute, with a goal to increase the number of Black checkwriters in venture. This curriculum-based program has graduated 100+ fellows, including eight Operator LPs to date.

Leyla, my friend, I couldn’t be more grateful for all that you’ve contributed to building the heart, soul, and engine that is Operator Collective. Nor could I be more proud of how you took on the venture world and made lasting change during your time as an accidental venture capitalist. I can’t wait to see what you do next and am excited to be right by your side as you keep shaking it up.

5 actionable tips for DEIB recruiting

Countless research shows that diverse teams are better-performing. Harvard Business Review has demonstrated that what’s good for diversity is good for organizational performance. And according to global talent solutions firm Allegis Group, a diverse workforce and inclusive culture is one of the most in-demand asks from candidates. That’s important to recognize, since we all know how competitive it is to attract talent right now.

As the co-founder of a recruiting software platform Searchlight.ai, I have a lot of conversations with people and talent leaders. What’s become clear is that creating a diversity, equity, inclusion, and belonging (DEIB) strategy is a top priority for any company that hopes to be competitive. Many of these businesses are turning to recruiting as the place to start moving the needle on diversity.

In the words of Michael Kieran, Operator Collective LP and head of talent at Tray.io, “Recruiting is the front line where we can make the most impact on diversity. It’s our responsibility and a privilege to put DEI strategy in place and then tactically execute to improve what hiring practices look like.”

Read on for five actionable recruiting tips that will bring you closer to your DEIB goals.

1. Set one data-driven target at a time

Being focused is critical to changing behavior quickly. At Tray.io, Kieran says he cuts through the noise by choosing a main single target to aim at. His current metric focus is the percentage of the employee base that is non-male and non-white.

Be data-driven when crafting your diversity targets and customize them based on your company’s customers and mission. Zapier’s recruiting operations lead, Supreet Hundal, recommends investing in data hygiene and talent analytics software to measure demographic numbers. “Without data, it’s hard to know where we actually are against where we should be,” Hundal shared. “But with benchmarks, we can create targets and align on which groups to partner with, [and] which communities to invest money in.”

2. Define candidate success criteria based on competencies and capabilities

Jeff Diana, chief people officer at Calendly and former recruiting leader at Atlassian, says, “One of the fundamental truths about human psychology is that we’re drawn to people who look like us. We also know that organizations today are not diverse, especially in leadership. So it’s a fact that, despite our best efforts, there’s already all kinds of bias in our organizations.”

One way to counter these natural biases is to define objective, competency-centric hiring criteria. “Defining success criteria is key to successful hiring – period,” Diana says. “Getting scientific on the capabilities that make people successful at our organization helps us avoid screening people out on superficial attributes.”

3. Reinforce fair and consistent evaluation methods

While at Google, SVP of People Operations Laszlo Bock found that interviews were not actually that predictive of future performance. Recruiting teams need to get creative and look for new ways to accurately assess which candidate is the best fit for the job based on the objective success criteria set in step two.

“We must use frameworks and rubrics to keep our ratings consistent,” John Foster, chief people officer at Truecar, says. “Using a disciplined, pre-defined set of factors with clear definitions will result in less biased decisions and more objectivity. It will allow us to overcome gut instincts with numbers and science.”

One way to counteract subconscious bias is to corroborate what the candidate highlights in their resume and interviews with their prior on-the-job contributions. LinkedIn reports that reference checks can make your interview process more predictive. When reference data is compared with resume screens and interviews, hiring teams can confirm or disprove assumptions from interview feedback.

Some tips for fair and consistent evaluation include holding structured interviews, building diverse hiring panels, leveraging talent software, training interviewers, and building reinforcing mechanisms into your process.

4. Actively source from historically excluded communities, don’t rely on inbound

Once you’ve set your candidate success criteria and evaluation process, you’re ready to screen your pipeline. But the resume screening process for inbound applicants is often rife with inconsistencies that can lead to discrimination. By investing in outbound sourcing, you’ll have an ethical path to getting more diverse candidates into your funnel.

Sourcing is also a great way to remove barriers that have traditionally faced underrepresented groups. To bolster this strategy, experts recommend tapping into new sourcing channels, nurturing relationships with communities that work with historically excluded groups, and investing in software to support your sourcing strategy.

5. Tackle post-hire metrics together – especially quality of hire

“Sometimes recruiting is silo’d from the rest of HR, but that’s the craziest thing ever,” Diana believes. “You have to cross over to HR and see which candidates are actually successful. If recruiting doesn’t measure post-hire outcomes like quality-of-hire, you can’t show the positive impact that increasing diversity has on the business.”

Quality-of-hire (QoH) measures the value a new hire adds to your company, and gives recruiting teams data-backed answers around which candidates become top performers and which skills and competencies are predictive of performance during the interview process. Yet, how to properly track QoH is a long-standing debate amongst recruiting and HR leaders given the difficulties in effectively measuring it.

Despite this history, QoH is powerful for increasing DEIB for two reasons. First, it can scientifically show the benefits of hiring diverse talent. Secondly, by understanding which competencies and skills predict on-the-job experience, teams avoid over-indexing on prestige markers and familiar credentials. It’s not surprising that nearly 40% of talent acquisition leaders list tracking QoH as their top priority.

DEI is DNA

Brandon Sammut, chief people officer at Zapier, says, “DEI is DNA.” The world’s leading companies know this to be true, but making a sea change takes time. I believe that the quickest path to action is to embrace the reality that all humans have biases. Designing recruiting systems with the five core elements I’ve shared can create an engine for faster, fairer diversity outcomes.

Anna Wang is the co-founder and CTO of Searchlight, a critical piece of talent software for companies serious about hitting their diversity targets and increasing talent density.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or on Twitter and LinkedIn.

Operator Spotlight: Marketing and eCommerce leader Richelle Parham

Looking for practical help and advice on an operational area that may be outside your realm? Each month we spotlight one of our talented operators, who’ll share their expertise and offer insights and ideas that may help improve your own operations. This month we spoke to Universal Music’s Richelle Parham.

You’ve just joined Universal Music Group as President of Global eCommerce and Business Development. Can you walk us through your new role? 

RICHELLE: I am so thrilled about the new opportunity with Universal Music Group (UMG). The role is overseeing UMG’s global eCommerce strategy and business development across the company’s iconic labels, publishing company, operating units, and territories. I am able to use my eCommerce, consumer marketing, audience growth, business development, and direct-to-consumer experience to elevate UMG’s artists and drive the UMG vision of a holistic fan-centric ecosystem that complements partner platforms.

You’ve had such an impressive career in marketing and strategy spanning consumer, tech, and most recently venture capital. What inspired the move to the music industry?  

RICHELLE: I have had a tremendous career and a lot of fun! I was not looking for a new role, however, the more I learned about Universal Music Group and the opportunities to drive eCommerce in more impactful ways (with music as the foundation), the more excited I got. A lot of my focus is around building an ecosystem that connects fans to the artists they love, whether it’s through offline or online experiences, value added content, or merchandise. What has been great about my career is the expertise that I have gleaned over the years can be applied to most industries. I love music, and now I’m able to take my extensive eCommerce, marketing, and consumer knowledge and apply it to the music industry.

What advice would you give someone looking to navigate their next career move into a new industry or function? What are some strategies for evaluating new opportunities? 

RICHELLE: The advice I often give is to be a master in your field and understand how what you do well applies to the new industry you’re interested in. Take the time to learn the industry, ask good questions, and make strong connections.

One of the lessons I’ve paid attention to in my career is not being afraid to learn something new and ask questions. A lot of people feel like asking too many questions makes it seem like they don’t understand. But I actually find that the person in the room who’s willing to ask questions is seen as inquisitive, creative, and innovative. They’re able to see the world in a different way. It’s so critical to have a healthy curiosity and hear other people’s perspectives and viewpoints.

You’re also an active board director at high profile companies like Best Buy, Elf, and LabCorp. Do you have any tips for operators seeking their first board position? 

RICHELLE: It’s probably the same advice as changing industries. Be very clear on how your experiences, expertise, and background can be beneficial for the board and the company. Leverage your network to make connections and get to know the executive recruiters who focus on board opportunities.

It’s also important to build your legacy every day. You have to put points on the board and have key accomplishments that people will remember. Make sure you think about the impact you’re going to leave on any business you work with. 

In your opinion, what are some ways the tech and venture industries could do a better job of empowering the next generation of diverse leaders?

RICHELLE: Companies have to be deliberate about bringing in diverse leaders and elevating diverse employees. The power and opportunity comes when you have diversity of race, ethnicity, gender, and thought in the room. 

For example, from a venture perspective, we built diversity right into our strategy upfront in my last position at West River Group. Each one of our sectors was co-led by a man and a woman, because we really wanted to create change. We were doing something different by investing in the folks that don’t generally get the money. If you have diverse people allocating capital, they will allocate to diverse teams.   

AOC often talks about the skills she picked up as a bartender, and others talk about what they learned working retail. What were some of those formative jobs for you?

RICHELLE: When I was a student at Drexel University, I was also interested in fashion and did three 6-month co-op jobs working for Valentino in New York. I was the Assistant to the National Sales Manager. One of my roles was being responsible for placing the multi-million dollar orders for major retailers like Neiman Marcus and Saks Fifth Avenue. One order would take days to input into the computer system because, for example, it would be an order for all the Neiman Marcus stores across the country. I would input the order, then I had to check it two times before submitting it. From that role, I learned how to be incredibly detail-oriented and I learned how to hone my process management skills. Those skills have been essential throughout my career journey.

What’s your secret super power? 

RICHELLE: I am a great connector. I pride myself on being a good listener and through hearing people’s stories figuring out who they need to know. I love connecting people who can open doors for one another and support each other. 

For even more great wisdom from Richelle, check out her recent interview on the Potential to Powerhouse podcast.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or on Twitter and LinkedIn.

Searchlight: Unearthing new insights to hire top performers

Searchlight team

The company: Searchlight

Searchlights performance-driven hiring platform helps companies leverage references to scale winning cultures. The company’s scientific reference assessments evaluate candidate competencies and working styles in a way that is faster, more accurate, and less biased than interviews. Over time, Searchlight’s talent analytics create a dynamic model of a company’s top performers. This closes the loop between recruiting and hiring outcomes, and teaches organizations how to improve diversity and quality-of-hire.

Why you should pay attention 

Boards always ask their CEOs and leadership teams: “How do we know we’re hiring the best talent?” There’s been no data-backed way to answer this question, until now. Searchlight is built by operators for operators who recognize that measuring and improving hiring quality is a competitive advantage.

Forty-six percent of all hires fail within their first 18 months, costing an organization 1.5-2X their salaries in compensation, lost productivity, and missed deliverables. Teams that rely solely on credentials and interviews are unable to get the full picture of a prospective hire before making their decision. While interviews aren’t predictive, feedback from prior colleagues can be. References, if used correctly, are a secret weapon to hiring better and building a structured trove of data to drive a vast array of smarter talent decisions.

The details 

Searchlight’s solution starts with a reimagined reference check process that is predictive and easy-to-use. The platform assesses candidates objectively, putting greater emphasis on reliable indicators of top performers like real-world feedback on strengths and weaknesses that might not come through in a resume or interview. Searchlight’s visually compelling reports deliver consistent, structured, and honest data that changes the way companies make hiring decisions.

Using Searchlight, companies like Zapier, Discord, TalkDesk, Coda, Snapdocs, and Udemy are saving thousands of hours, reducing time to hire by 45%, improving their quality-of-hire by more than 20%, and increasing the number of hires they make from underrepresented backgrounds. But the team is just getting started. Beyond references, Searchlight aligns recruiters and hiring managers and surfaces predictive recommendations for future hiring. With verified data on historical hires over time, the software suite provides intelligence at both the start and end of the hiring process, so it can continuously improve hiring outcomes.

Why we’re obsessed 

In order to create a more diverse and equitable future, companies need to rethink traditional approaches to hiring. Thankfully, there’s still tons of untapped potential in the recruiting process, especially around talent intelligence. Searchlight provides both the data and analytics to help recruiting teams hire more top performers—without adding steps to the recruiting process. 

The key to merit-based hiring that moves the needle for diversity is uncovering new data points (outside of credentials) that offer a holistic understanding of a prospective employee, and then tying them to real performance outcomes. We believe Searchlight will set a new standard for companies serious about hitting their diversity targets and increasing talent density.

Searchlight’s origin

First-generation Asian American twins Anna and Kerry Wang decided to create Searchlight soon after they graduated from Stanford, with bachelors and masters degrees in computer science and artificial intelligence. During their own job searches, they saw several shortcomings in how organizations evaluated their (nearly identical) resumes—noticing that the unique competencies, working styles, and strengths that set them apart were overlooked. 

Natural entrepreneurs, they set out to fix that by making references a central part of the hiring process and started out their journey with Y Combinator. They’ve since been recognized on the Forbes 30 under 30 list

Get involved

Curious to see what your next reference check will find? Join Searchlight’s candidate waitlist so you can set up your own profile. If your company is hiring, give Searchlight a try and let us know what kind of difference it makes.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or by connecting with us on Twitter and LinkedIn.

 

If you do benefits, you need Noyo

The company: Noyo

Noyo is the company transforming data exchange across the insurance ecosystem by delivering the universal API for embedded benefits. By building the connections gateway that allows for fast, accurate, and secure data exchange, Noyo is helping benefits software companies and insurance providers deliver next-generation benefits experiences to their customers. 

Why you should pay attention 

Co-founders Shannon Goggin (CEO) and Dennis Lee (COO) are leading a team that’s powering the age of connected insurance, where it’s as easy to access benefits as it is to connect to a bank account or make a payment online. Leading insurers including Unum, Humana, Ameritas, Beam, Principal, Sun Life, and Brella are using Noyo APIs to power their data exchange and meet the demands of the digital age. The industry’s most innovative benefits software platforms, including Zenefits, Rippling, Namely, and Sana, are using Noyo to deliver a new era of seamless benefits experiences. But the biggest beneficiaries of Noyo’s innovation are the people that these companies serve, consumers who can now expect insurance data to move freely, giving them easy access to the benefits they need, when they need them. 

The details 

Noyo’s APIs for benefits administration cover the entire lifecycle of a policy. APIs for member enrollment changes facilitate sending transactions, receiving confirmations and automating accuracy. The  verification API helps principals confirm enrollment status for any member at any time. And the Noyo 360 end-to-end APIs bring benefits full circle by streamlining installation and renewal. Noyo has delivered a fast, intuitive developer experience that lets leading insurers and benefits platforms redefine what’s possible for open enrollment as they transform their digital strategies and accelerate growth. 

Why we’re obsessed 

Health insurance is a trillion-dollar industry running on disconnected and outdated systems. Technology is reshaping how people engage with health insurance, with a new generation of software emerging to modernize how people shop for, enroll in, and manage their coverage. Behind the scenes, though, insurance is administered by a tangle of disconnected systems stitched together by manual processes. Noyo is upending this status quo by building the infrastructure that will power modern insurance distribution.  

Get involved

Whether you’re building, upgrading, or scaling a benefits offering, Noyo can help you get there. Want to lead in the age of connected insurance? Get started with Noyo

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or by connecting with us on Twitter and LinkedIn.

How to get started with angel investing

*WARNING* What I’m about to say about angel investing will annoy the heck out of professional investors and rightly so. I am an amateur shooting from the hip, but I’m happy doing so. 🤠

Investing money is just one type of investing to me. It’s no different than spending time, sharing your brain power, advising, supporting, or advertising. All of these things are limited resources. 🧠 When I was at Microsoft, for example, the “investing” I did was in recruiting, onboarding, and development: I was a person you could go to for hugs and cookies 🍪, cheerleading 📣, and championing. I have always tried to put my resources where my mouth is, to solve problems worth solving. And those are to create more time ⏳, freedom 🆓, quality of life 🥂, and joy 😄 for more people. Isn’t that what tech is all about, to create tools for people to solve problems?

To me, angel investing is enabling a person with an idea to 3D-print it herself. I particularly enjoy being an enzyme 🧬, a catalyst 🧫, that first follower who endorses and lends credibility to a thing. Therefore I invest in people doing things I think are cool and making the world be more the way it ought to be, and where I think I can be useful. It is a relatively new tool in my toolbox 🧰, one I started using in 2019 when I really began digging into startups and entrepreneurship. I wanted to learn from people who were doing what I dreamed of. 🏫 Plus it seemed a great way to give, not just to take. But it’s also direct and visceral. 👼🏼  Many people with world-changing ideas can’t afford to quit their day jobs and work on their ideas full-time — not without money. And it’s hard to raise money unless you’ve already raised some money. 💱 

To be an early-stage people-and-idea investor is to be a gardener. 👩🏻‍🌾 And I don’t mean growing blackberry bushes, which grow here in the Seattle area no matter what you do. It’s more like olive grove or grapevine gardening. 🍇 You don’t just plant and harvest. You have to cultivate and tend, age and develop, and support and water for years. It takes a long time and you need to love it. 🌸

My biggest tips for operators who want to get into angel investing:

  • Figure out what problems drive you crazy and what areas you love, and invest there.
    You’ll have better intuition and help more on things you care about and understand. You are also more likely to connect well to people working on those things. 💖
  • Find or build a community.
    Join an existing angel syndicate, a group or conference (like Seattle Angel Conference or Alliance of Angels), crowdfund (Backstage, Hustle, and Rarebreed have them), or pull together a group of friends who want to get into it too. 🤝🏽
  • Make an investment and put it in your LinkedIn/Twitter bio.
    You’ll bring awareness to the thing you invested in, but it will also make you visible to those looking for investors. Try it. Seriously, put “Angel Investor” in your activity list on LinkedIn and see how many messages you get from founders looking for investors who find you in a search. 🤯
  • Leverage your superpowers.
    Part of investing is to change the probabilities of good outcomes. Anything you can do to nudge one bit left is helpful and it adds up. So why not invest where things you are great at and come easy to you can change the result for the better? 🦸‍♀️
We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or on Twitter and LinkedIn.

 

Operator Spotlight: UpLift Co-Founder & CTO Laura Butler

Looking for practical help and advice on an operational area that may be outside your realm? Each month we spotlight one of our talented operators, who’ll share their expertise and offer insights and ideas that may help improve your own operations. This month we spoke to UpLift’s Co-Founder & CTO Laura Butler.

You spent 22 years as an engineer and technical fellow at Microsoft during some incredibly pivotal times. How did your time at Microsoft help you develop as a leader? 

LAURA: First, I got to work at the company during an incredible time in the early 1990s when mission was so front and center to everyone. We were changing the world by expanding the set of people who had access to top-notch tools and information through devices by orders of magnitude. I learned the value of a great mission and vision; they energize people. They help teams through tough times to know why they’re slogging and how it matters. They guide more coherent decisions, features, and products. 🔭 

Second, I got to see great leadership in action during the early days of Windows and Office. People such as Brad Silverberg, Jodi Green, David Cole, Rich Tong, Julie Larson-Green, and many more. Space is infinite, right? ♾ The set of stuff that works is the interior of a cube and that’s finite. Unfortunately the set of stuff that doesn’t work outside that cube is infinite. That’s to say that learning what not to do and when not to do it only goes so far; being able to observe how incredible people operate and how they solve problems is huge. 🕵🏾‍♀️

Third, rage-quitting after a reorg in 2000 was a transformative moment. I had to grow up, figure out what really matters to me, and develop a philosophy. You can’t be a good leader, especially an engineering leader, without these things. When you’re an engineering leader, part of your job is to engineer the engineering culture. Before I quit the first time, if I’m being honest, my approach to leading/managing was like a refrigerator light 🔦.  Everybody around me was there to turn on when I opened the door because I needed something, and it wasn’t my fault if they were illogical or unable to understand my genius.  

You had a hand in the user interface (UI) of many of the Microsoft programs and apps we use on a daily basis. Looking back on it now, what was the environment like for engineers? 

LAURA: Computing resources were very tight in the 1990s. 🧮 You couldn’t work on the UI and not be deeply familiar with memory usage, CPU, I/O, and more. Rendering used math front and center:  rasterops and vectors and sets and matrices. Everyone, regardless of specialty, had a solid fundamentals base. There was less silo’ing, more respect, and a lot less “you’re just a front-end engineer, while the real programming is back-end services” kind of elbowing. 👩🏽‍🔬

You absolutely had to be able to debug up and down the stack to make things work, and work well, in Windows ‘95. On top of that, you had to intuit what app developers were doing and how they were doing it so you could solve compatibility problems your changes caused. (You would not believe the number of bugs that increasing the width of a line from 1 to 2 pixels can cause. 🐜)

Because releases were slower and computing resources were tighter and the cost of correcting errors in shipped software was higher, engineering teams invested a lot more in design and architecture, documentation, tools, and training. It was part of the job to keep things up to date, and we had support from technical writers, product support, and others. 📝

Today you can try and test things in minutes, and if you don’t cut corners, you can right roll back the changes in minutes when you find out how badly you’ve broken things. That’s wonderful; it gives such space and freedom to experiment and learn. But the flip side is that the engineering rigor muscles have atrophied. Distributed services have layers of resiliency and robustness — as they must — but some of that is at the expense of debugging and truly fixing problems, rather than putting band-aids on them. 🩹

Here’s a photo from the launch of Windows ‘95 with some state-of-the-art laptops. We look like a New Wave band!

You founded UpLift Group in 2020. Tell us about UpLift and what prompted you to start a business. 

LAURA: Thank you for using the word business! I’m proud that we have revenue from people who aren’t related to us, don’t even know us, and choose to pay us. 📈

First let me explain what my startup is doing. UpLift Group is building the CarFax and Consumer Reports of condos. We want happy owners in healthy Homeowner Associations (HOAs). Our mission is to provide quality information and accessible expertise about condo and townhome HOAs for individuals. 💪

So how did we get here?

Carol, my co-founder and CEO, and I knew in 2019 we wanted to found a company and we wanted to do it old-school: bootstrapping and starting from square 0 for the learning and experience.🛠  

As part of making changes, I Marie Kondo’ed my life. I had a house that was too much work to care for, plus had tripled in value, so I sold it and bought a condo. Condos are supposed to be easy, right? They make great homes for people who don’t have the time, desire, ability, or money to take care of a stand-alone house. They offer amenities, security, logistical efficiency, and access to opportunity and culture in urban areas. 🌆

I almost bought a condo that I would have regretted immediately due to pet restrictions 😿 and an upcoming special assessment. 💸 I fell in love with the space and didn’t even think about the HOA. I didn’t know what I didn’t know. HOA docs are immense and inscrutable, but they are also often incomplete, out of date, or just plain wrong. So even if I’d had a clue, I would’ve had difficulty establishing the facts. 😱  

It turns out that HOAs are hard. Understanding them requires mastery of arcane finance, governance, and maintenance. Fortunately Carol is a world-class expert on condo/townhome HOAs. She’s owned many condos herself and served in every board position. Plus she’s an economist with a background in data science and econometrics, specializing in utilities and public policy. You couldn’t manufacture a better person in a laboratory if you tried. 🧪  I’m now a happy owner of a different condo because of her. 

So a lightbulb went off 💡 and we decided to focus our startup on HOAs. The more we dug in, the more convinced we became that there were huge gaps, huge problems, and therefore a huge opportunity to help people and create value. Our core service today is a Resale Review, scouring the indigestible stack of material a buyer gets about an HOA as part of resale disclosure, analyzing it, extracting what matters, and making it easy to understand. We help buyers and their agents decide whether to go through with a purchase, give them data that helps with offer negotiations, and ensure they’re prepared to be owners. We provide peace of mind. 🧘‍♀️

As a bonus, here are a few ideas we didn’t pursue. If somebody out there wants to run with one of them, hit me up for details and possibly an angel investment 🙂

  • Patroness 🎨🎻… a way to support artists, actors, and musicians by letting them stay for free in your home, buying them meals, or hosting an event in exchange for tickets.
  • Carma 🚗👍🏼… a mobile app you can point at a license plate and then send thanks or a small gift to the driver when they do something nice (like let you out of a parking garage on a busy street)
  • Lo-cat-or 🚁🐈… rentable drones with infrared, microphones, speakers that maybe also can emit treats you can use to find your lost pet

The number of technical women founders and CTOs is on the rise. How has the landscape changed for technical women over your career? 

LAURA: It’s come back around to where it started, even better, and that’s a good thing. When I joined Microsoft, there were more women in programming, more women engineering managers, and more women in senior positions. There was no engineer cookie cutter stamping out the same shape. The industry was creative problem solvers and misfits figuring things out that hadn’t been figured out before. 👩🏿‍🎨 

Somehow it got middle-aged, pompous, exclusionary, stratified, and unwelcoming around 2000. 🏹🗡 I’m not sure where the zero-sum winners-losers kind of behavior came from. Insecurity must have been a factor. Maybe getting more removed from real purpose and humans was a factor too. Programming became a priesthood and cult of its own, instead of a toolset. 🏛  In any case, this impacted a whole lot of people besides women. Who’d want to study computer programming if it was all or nothing, you didn’t think you could pursue your other interests, and you didn’t look like the people already in the industry? 🚫

I love how less binary and more quantum programming has become in the past 5-10 years.  Open source, SaaS, and low-code are here to stay. If you have an idea, there are multiple ways you can build it. You don’t have to get a CS degree. The whole “technical” vs “non-technical” distinction is less relevant and clear every year, which is fantastic. It’s ever more about making things to solve problems and solving problems to make things, as it should be. 🤗

In your opinion, what are some ways the tech and venture industries could do a better job of empowering the next generation of diverse leaders?

LAURA: I feel like the “adventure” isn’t as front-and-center with tech and venture as it should be. Of course there is risk. Nothing ventured, nothing gained. But risk is something you manage with action like support and advice, not just assess with data. The point of risk is reward. Following the pack and staying safe are not how you win.  They are defense not offense. 🥅

Tech and venture folks should examine Cirque du Soleil, martial arts, ice skating, gymnastics, rock climbing, and skyscraper construction. Case studies in these areas should be taught in business school. All these areas require failing a lot and are arenas where failing can be catastrophic. So rationally they invest in safety equipment and practice over and over again handling errors and problems to recover as safely as possible. Tech and venture ought to do the same and build virtual harnesses, trampolines, mats, ropes, self-arrest techniques, and rope teams. 🤸🏽‍♀️

Why does this matter? Because great management and leadership take practice and development. And underrepresented groups have less room to fail. More visibility, more pressure, less resources, and fewer tools to use to mitigate slips and falls = less chance of succeeding and more damage when problems arise. If the industry truly wants to invest in people, it should invest in the equivalent of safety equipment and padding to minimize the bruising. 🦺

AOC often talks about the skills she picked up as a bartender, and others talk about what they learned working retail. What were some of those formative jobs for you?

LAURA: I went to college young, plus I was a bookish nerd, so I never had a real job before joining Microsoft as a summer programming intern in 1989. Then I got paid to sit in front of a computer with air conditioning, play Tetris, and blow things up with dry ice inside of plastic bottles, all while getting unlimited free soda and snacks. It was awesome! But I didn’t learn practical things. Between school and Microsoft I was in a cocoon. 🐛🦋

More practical knowledge and experience honestly came after I left Microsoft the first time in 2000. I was fun-employed for 6 years and decided to try things I had only read about.  Adventure travel and cooking were really formative. The former because of a mindset and skill set that carry over so well to innovation. You don’t know exactly where you are going and there aren’t paved superhighways. 🥾🗺 So you need to figure out how to go the distance sustainably and you better enjoy it. The latter requires logistics by restaurant staff at a level that puts engineers to shame. Peaks are crazy high, time is tight, it’s got to be a personal and customized experience, and it’s emotional for your customers. 👩🏿‍🍳🔪

So if your engineering team is complaining about how hard it is to get a feature done and shipped on a schedule, have them spend a Friday night as a prep chef or a line cook at a restaurant that handles a lot of pre-theater traffic. 😰

What’s your secret super power? 

LAURA: Active contrarianism. If you need to lead a rebellion and overthrow an evil space empire, I am your princess general. 👹🌌👸🥊

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or on Twitter and LinkedIn.

Make your SaaS portfolio more Productiv

The company: Productiv

SaaS is everywhere these days. But the awesome proliferation of SaaS applications has also added an intense level of complexity to our tech stacks. Enter Productiv, a SaaS Management Platform that gives IT leaders unparalleled visibility and control of their app portfolios. The platform provides a unified view of SaaS apps, enabling smarter renewal decisions, more intelligent license allocations, and stronger application adoption. With Productiv, businesses are improving the employee software experience by maximizing application value and containing risk within sprawling IT portfolios that can involve hundreds, if not thousands, of apps. 

Why you should pay attention 

Some of the world’s most innovative companies including Uber, Zoom, Okta, Box, and many more are using Productiv to enhance their SaaS planning and governance. Typical customers see 30% in cost savings on renewals thanks to the detailed software usage and engagement data provided by Productiv platform. Productiv customers have used the platform to discover that a typical 43% of apps used in the organization are shadow IT. On average, Productiv saves companies 38 hours weekly across IT teams. 

SaaS is vital to every modern business. As the number of SaaS apps continues to grow, so do the challenges IT has in managing them. Productiv is giving companies new ways to keep their SaaS portfolio under control, stay agile, save money, and make transformational decisions.  

How it works

Productiv gives businesses details about application engagement — everything that happens after the employee logs in. This allows IT leaders to see and analyze exactly how applications are being used. These insights can also be easily surfaced to IT’s business partners across the organization, delivering a single source of truth to stakeholders across the company. Productive equips leaders with actionable insights and smarter recommendations to strategically negotiate upcoming renewals, seamlessly allocate existing licenses, and improve employee engagement.

Why we’re obsessed 

While precise estimates of the SaaS market vary, everyone agrees on this: it’s worth hundreds of billions of dollars and it’s experiencing double-digit growth. Productiv co-founders Jody Shapiro (CEO), Munish Gandhi (COO), and Ashish Aggarwal (CTO) have built an incredible workplace that has attracted a stellar team — including alumni from leading innovators like LinkedIn, Facebook, Google, Slack, and Amazon — to deliver a data-driven platform that helps IT leaders get a handle on their enterprise SaaS portfolios. The company has built a powerful solution and is already seeing incredible traction with analyst accolades and a customer roster full of A-listers who love the product. 

Get involved

It takes 10 minutes to set up SaaS Management with Productiv. Unify your sprawling portfolio, simplify operational workflows, and get the intelligent data you need to unlock employee productivity. Get started now for free.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or on Twitter and LinkedIn.

 

4 tips for designing your org’s post-pandemic transition plan

In 10+ years in SaaS, I don’t recall another time in which people practitioners have been so cosmically overwhelmed. When COVID hit, HR leaders had to modify their people and culture strategies seemingly overnight, leading their organizations through multiple traumas and crises. And it hasn’t stopped since; recent months have continued to bring unknowns. As we explore new ways of working (like hybrid work structures), there’s the added complexity of the employee post pandemic existential crisis and an ongoing raging war for talent

Despite how important the post-pandemic transition is, more than 60% of executives still don’t have a solid plan in place to support their employees through it. Smaller organizations in particular – those without a dedicated HR presence – are searching for strategies that align both to progressive practices and their goals around culture. Here are 4 things to think about as you work to cement your post-pandemic transition. 

1. Please don’t call it a “return to work.” 

The great philosopher LL Cool J once said, “Don’t call it a comeback. I’ve been here for years.” It’s a lyric that’s been living rent-free in my brain for the past few months. 

That’s because every HR leader I’ve spoken to lately has had the same reaction to the phrase return to work: Annoyance and frustration. I’ve had the same reaction, and it’s largely just a syntax issue. Return to work may flow off the tongue, yet it implies that employees have been… not working

The reality of the pandemic year is that many employees have been working even harder than usual, while also balancing the seemingly impossible conditions and new responsibilities. It feels wrong – and condescending, honestly – to imply that these employees are returning to work, as if they’ve been on vacation this whole time. Words matter; as your company defines its workplace model, be sure to choose yours carefully. Before rolling out your communications plan company, ask your DEI leader, ERG, or even simply a diverse group of employees to provide thoughts and feedback. 

2. Get up to speed on Equitable Organizational Design

A strategic approach I endorse is one I first learned about from Operator Collective LP and Culture Amp Director of Equitable Design and Impact Aubrey Blanche: Equitable Organizational Design. While leaders focus on building a diverse and inclusive culture, this model encourages them to evolve their design practices towards equity and belonging. As Aubrey puts it, “Moving from inclusion to belonging is critical because it’s moving from ‘We created a space, and it’s fine if you show up,’ to ‘We created a space for you,’ or ‘We created a space with you.’”

Incorporating practices from equitable organizational design impacts not only the employee experience, but also the company’s bottom line. Companies mandating a return to the office are now watching employees quit, rather than give up their work-from-home lifestyles. As Lars Schmidt recently tweeted in response: “You thought recruiting was hard? Retention will be the biggest challenge companies face for the next several years.” Indeed, it is a whole new frontier.

Regardless of where your company lands on Equitable Organizational Design, incorporating some of the approaches SAP, Microsoft, and others took to research their strategies before rolling them out may help you avoid getting caught on your retention strategy heels.  

3. Leverage open-source resources to build your strategy

There’s no baseline practice for navigating the post-pandemic transition. When I co-founded HR Open Source in 2014, our aim was to create a free, peer-based community where HR leaders could open their playbooks, particularly where best practices hadn’t been defined. Today more than 11,000 practitioners across 70 countries share learnings, ask advice, and publish their work to advance everyone. This online community is now one of many that share free resources for everyone to tap into. Here are some places to start with regard to your post-pandemic transition:

4. Share your plan

You probably saw this tip coming from me, and I’m happy to say that this is already happening at a higher frequency than ever before. In the months ahead, I hope companies and leaders will continue to share not just what they are doing, but how they’re doing it on open source forums and communities.

By working out loud and sharing our learnings (and mistakes!), we can all move forward faster and better than before. It’ll also help us to define more progressive practices for the proverbial future of work that’s already at our doorstep.

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or by connecting with us on Twitter and LinkedIn.