Why we’re obsessed with Guild Education

The company: Guild Education

Guild Education is a female-founded, Certified B corporation that’s on a mission to educate America’s workforce. Guild seeks to do well by doing good, offering a full-service platform that lets companies connect their employees to amazing education benefits.

Why you should pay attention 

Companies like Walmart, Disney, Discover, Lowe’s, and Chipotle have already realized jaw-dropping results with Guild’s end-to-end platform for education benefits and tuition assistance. (Disney reports record-breaking engagement with its Guild offering, while Chipotle reports 90% higher retention among employees who participate in the education benefits program. Whoa!) 

The details 

There are 88 million Americans who need upskilling or reskilling in order to compete in the future of work (64 million of whom haven’t completed college). Those were some of the facts compelling co-founders Rachel Carlson and Brittany Stich to shake up the traditional model and create a business for change. The resulting company, Guild Education, tackles the problem by helping Fortune 500 companies provide debt-free pathways to college for their employees. 

Why were obsessed 

Guild turns the traditional tuition reimbursement model on its head, reimagining a system that’s well meaning, yet antiquated and ineffective. To do this, Guild connects companies to a network of nonprofit, accredited universities and learning providers curated to provide the best outcomes for working adults. Their innovative tuition assistance model allows students to pursue associate’s, bachelor’s, and master’s degrees, as well as a wide variety of certificates and credentials without having to pay *any* upfront costs. (Students can also participate in English as a second language, high school completion programs, and college prep.) By removing that initial cost barrier, Guild’s model allows more employees to take advantage of the benefit + helps more employers realize a positive impact.

How it works

First the Guild team works with individual companies to build a customized education program and benefit policy that supports the company’s strategic goals, including objectives for recruitment, retention, and upskilling. Once the program is in place, Guild offers a team of coaches that works with individual employees to identify the right programs for them, then help with enrollment, coursework, and accountability. Completing the circle, Guild’s automated platform features dashboards and analytics to help companies track engagement, performance, retention, and overall results. 

Get involved

Ready to reimagine your company’s education benefits and increase employee retention, engagement, and success? Great idea – Get in touch with Guild Education now.  


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

Everything you wanted to know about angel investing, but were afraid to ask

Thinking about angel investing? It’s a worthy way to spend your time and can be quite lucrative if you choose the right opportunities – but there’s also a great deal of risk. After my previous career in product at Salesforce and PayPal, I turned my technical experience into a sidegig as an advisor, where I reveled in helping driven founders and their teams succeed. Eventually I became an early stage investor, joined the launch of Backstage Capital, and recently joined the launch here at Operator Collective.

Now that I’m 5 years in, I feel equipped to share some knowledge, namely the answers that would have helped me as I started out. Here are the most common questions I get about angel investing (and special thanks to Courtney Broadus for sharing her considerable expertise and perspective here too!). Got a question I missed? Please reach out

What is angel investing? 

Angel investing is the term used when an individual investor gives money to startups or early stage companies in exchange for an equity ownership interest. This is often done using a SAFE note, which is a form of convertible note, that gives you the right to purchase or “convert” to equity partial ownership in the company at a future date and/or when other criteria are met. 

How is angel investing different from investing in a venture fund? 

Angel investing is done on an individual basis and requires considerable due diligence. Investing in a fund is putting your money in the hands of the fund managers, whose job it is to vet the companies and use their expertise and network to make sound decisions. Venture funds can be lower risk than direct angel investments, depending on stage, diversification, and sector; however, the whole category is high risk.

How do I get started with angel investing?

Start by choosing a focus. Operator Collective and many of our members focus primarily on enterprise b2b, but others prefer different areas – such as consumer, healthcare, edtech, or impact investing. As you think, determine what you’d like to learn about through the process + what area you’re passionate about (in addition to returns). 

Next, look for opportunities. Be intentional – Your network may not know you have expertise in scaling, hiring, or a particular technology. So let them know you’re looking to invest and the area in which you’d like to focus. Research the VCs in various spaces; then connect and find out who they’re investing in. Finally, offer yourself as an expert to startups to build a network. Use your knowledge of the industry, products and services, operations, hiring, and more. Always look for opportunities to develop your own career, network, and knowledge while you work with founders.

How do I set a budget for angel investing?  

Angel investing is a high-risk investment. Consider it money you may lose completely – and if you’re not ok with that, don’t do it. Once you’re willing to accept the risk, parcel out a piece from the high-risk portion of your portfolio. You may want to set a yearly spend or a total spend, or you might simply consider each investment individually to gauge your level of interest. Whichever direction you choose, think about the total loss you’re willing to accept and stay under it for at least the first few years. 

How much is a typical angel investment?

There’s such a broad range of angel investments that there’s really no typical amount. Investments can be in some instances as little as $5,000 at the low end and $250,000 at the high end, though $25k and $50k are more common. Amounts are negotiable, based on what you can offer in addition to money (like your subject-matter expertise or network).

What if I don’t have a lot of capital to deploy? 

Get involved in other ways! What skills do you have that might benefit a startup? You can ask for equity compensation for advising a startup, which is usually a fraction of 1% over a 18-24 month vesting term (0.10 is common, 0.50+ is often only given to someone with deep domain expertise and/or devotes a material amount of time, 1% is unusual but not unheard of). You can also use your network as your investment – Whom do you know that could help a startup? 

How do I manage risk?

If you’re risk averse or don’t have time to do full diligence, consider co-investing with a group; this gives you coverage in a broader range of areas. Peer validation of your investments also helps you make a more informed decision. Use deal diligence to mitigate risk; but understand that at the early stage there often isn’t a lot of information available about the company and its customers, since many are pre-revenue, pre-product. Evaluating the team and its ability to focus and execute is often the strongest indicator you have to go on (vs trying to learn everything about the particular business).

What do I get out of angel investing?

It takes 7-10 years for most funds and investment portfolios to move to final outcomes (called exits). Typical exits are:

  • Late stage buy-out: Modest gains of usually 1.5x-3x
  • Pro-rata and follow on: The opportunity to invest more money in the next round to maintain or increase your equity stake
  • Acquisitions and mergers: Company gets acquired or merges with another, which can range from barely a 1x return to 3-4x typical. Most common type of exit.
  • IPO: Usually the very highest return, 4-10x
  • Company folds: Often you lose 100% of your investment, but usually you can write 100% loss off in taxes

How can I increase the certainty of a solid angel investment? 

Again, this is a high-risk form of investing with no sure bets most startups fail. But if you want to increase your chances of success, you’ve got to put in a great deal of time. Find deals you like from founders you believe in. Vet the companies as heavily as you can. Once you’ve invested, don’t just walk away check in, help out, stay involved. 

How do I find companies to invest in? 

  • Use co-investing groups and VCs you trust to build a pipeline
  • Join an angel investing group
  • Look for startup programs like accelerators and incubators, which often host Demo Days and offer opportunities for mentoring and advising
  • Network at meetups, conferences, and events
  • Start posting content on your channels to showcase your expertise 
  • Follow online content like newsletters and social channels
  • Talk to current and former colleagues, alumni groups, friends, and neighbors 
  • NOTE: Cold-call type leads can be more time consuming and challenging to sort though, especially if there’s not a reasonable connection to the founders or their industry 

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

Operator spotlight: HR leader Cindy Robbins

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 Cindy Robbins, a leader in the HR and Talent space.

You’ve been an HR leader for quite some time. What drew you to that career? What do you enjoy most about the People function? 

CINDY: It’s been a journey; I certainly didn’t start out saying I want to run HR one day. It was more of an evolution where I defined my path as I went along. I moved to San Francisco after college and started at a small consulting firm, where I learned several functions from recruiting to sales. I slowly realized I really enjoyed the talent function, which led me to a few different employers, including Excite@Home during the boom, Plumtree Software, and BEA. While at BEA, a friend introduced me to Erin Flynn, Salesforce’s head of global recruitment at the time. And once at Salesforce I was hooked. I loved being in a role where I could influence how to help employees feel valued. When I became President & Chief People Officer, I woke up every day glad for a role where I worked first and foremost for our employees.  

Why are people and culture so vital and defining for an organization? 

CINDY: Employees are redefining the rules of the workplace. If you’re an executive and don’t understand that, you’re in big trouble. Without a great culture, you don’t have an engaged workforce. And if your employees are not engaged and doing their best work, you will not make your customers successful. I remember the days when companies focused solely on the bottom line, but now employees want more. They want to be heard and want to be able to influence how the company’s values are defined and the actions behind them. 

It’s important to note that defining a culture happens over time. Think about something like workplace equality; no one was talking about that 10 years ago. So while it may not have been part of a company’s original DNA, it has to be there now. Values change, and every CEO, board member, and leader needs to listen, ask questions, and seek advice on how to adopt the right behaviors and values that drive the company culture forward over time. 

A lot of companies have been in the news recently for their negative cultures. How does an organization repair a negative culture? Is it even possible?

CINDY: I do think companies who run into negative culture experiences can turn it around. It takes leadership, trust, accountability, and transparency, and it has to start at the top with the CEO, leadership team, and board. Companies have to prioritize people and culture, and not just with nice words in a presentation. A culture is defined via actions and behavior. 

If you look at some of the companies with negative press, it’s important to note that it was often the employees who brought the issues to light – so it’s vital for every leader to LISTEN to all stakeholders and give them a safe environment to speak the truth. How do CEOs know what’s truly going on inside their companies? Not from just what they hear from the top of the ranks, but from the individual employees living it every day. How does the leadership team stay close to the truth, where messages aren’t cleansed as they rise up to the top? 

You’re known as one of the originators of the Equal Pay movement at Salesforce and beyond. How has that experience changed you + what are some lessons learned? 

CINDY: Leyla Seka and I both championed the Equal Pay movement at Salesforce. We did it because we were listening inside the company – listening to other women and to each other. Given that we were both in positions of power, we felt it was our responsibility to speak up. We knew we were taking a risk, especially when some were trying to tell us not to do it. 

I walked away with an awareness of what my role was – not just as the head of HR, but as a senior executive, a leader, a woman, and a Hispanic. I had influence, and I learned I could use it in positive ways. That’s important for every leader to know – You have to take risks to drive transformation. You can’t operate in silence. It’s doing good in the world that shapes who you really are.

And the other thing I learned was how much more powerful Leyla and I were together, two women just trying to make a difference for other women. We were proud of the outcome and the progress that was made, yet there is more work to do. I hope more companies, CEOs, and boards continue to highlight equal pay in their companies and provide the transparency needed around this critical topic.

What’s one amazing insight no one knows about HR?    

CINDY: HR is one of the hardest and least understood roles out there. HR organizations are often given the smallest budgets to work with, which is ironic given how important talent and people are to any company. It can be an organization that lives in constant frustration. But if you have a strong HR organization, you know it’s one built on trust – They are strategic thinkers and good listeners, show empathy when appropriate, and spread influence in a positive way. Many view HR as the police. I can’t speak for all HR orgs, but the ones I’ve worked with are full of genuine people who work tirelessly to make employees feel safe, engaged, and successful.

What’s the most epic way you’ve seen someone quit?

CINDY: Exits are not fun to watch. Ever. There are so many different types of exits within a company. Here’s one thing that always infuriates me: When an exit was caused because the employee had a bad manager. For example, when I would see exits because a manager never gave constructive feedback or had honest conversations, or when they prioritized company politics over doing the right thing. That makes made my blood boil.

What are some of the formative jobs you’ve had? Like AOC always 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?

CINDY: In high school I worked in retail, which taught me about the customer experience, working your way up from the bottom, and how to work with peers. It also taught me about the value of not just doing my job effectively, but the various behaviors it took to get the job done right. I think a job where you start at the entry level point is good for everyone. It teaches you about value, humility, ambition, and working with others. 

What are some business or non-business books you’ve enjoyed recently?

CINDY: I’m a big fan of anything by Brené Brown. Also Daniel Goleman’s Emotional Intelligence. And I love biographies; the last great one I read was Becoming by Michelle Obama.

What makes you roll your eyes every time you hear it?

CINDY: Any form of hypocrisy – when someone says one thing, but act differently. Also watching company politics win over doing the right thing.

What’s the one condiment you could never live without? 

CINDY: Salt. Can that count as a condiment? I love salty foods.

 

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

5 tips for building a thriving community from scratch

Those pics up there? That was me when I was a kid. I was the third of four children born to immigrant parents who still don’t speak much English. We were just trying to make ends meet, and life was pretty simple – food, school, and of course piano.

American ways were quite foreign to us. I still have to make my fingers into a “b” and a “d” to figure out where my bread plate and drinking glass go, and I was told Westerners weren’t trustworthy since they often said things they didn’t mean, like “Let’s have lunch” and not follow through. Or “How are you,” but not wait for an answer.

In 8th grade I was 4’6” with a home perm, heavy bangs, and thick glasses. We didn’t have much money, so I had three outfits; I wore each for two days in a row before rotating. There are kids who don’t mind these “limitations,” but I wasn’t one of them. I desperately wanted to fit in, but this was tough: even beyond my awkwardness, I was pretty unremarkable. I’m one of the few people I know who had virtually no activities in high school (I do know every episode of Gilligan’s Island, though). Plus, as with many families back then, parents didn’t talk about “adult things” to kids. All this means I didn’t really begin to interact comfortably with adults until I was about 30. 

Fast forward to today: I’m on my fourth startup, all of which have incredibly strong communities with networking that’s core to their success – ChIPs (5,000 members and 19 chapters around the world), RPX ($0 to $100M and IPO in less than three years), SaaStr (world’s largest b2b software community), and Operator Collective. How does someone so socially awkward build such thriving communities? In many ways not being a cool kid growing up was the perfect training ground for constructing communities and building startups. Here are five tips.

1) Find your niche

Communities and products succeed because they have a focus. People need a personal connection, which might mean choosing an area that’s ignored or overlooked. ChIPs started out hyperfocused on women in patent law (there weren’t many of us). Only after nailing that niche did we expand to women in law, tech, and policy. The venture world typically revolves around VCs and founders – so at Operator Collective, we put operators front and center.

Think about my awkward former self who just wanted to fit in. What if I’d had a community of Gilligan’s Island Aficionados Who Love Velour? I would’ve fit right in and had a core group to identify with. Find an initial niche or addressable market and expand from there.

2) Start with the bellwethers

The first thing everyone wants to know is who’s involved. Having not naturally been a people magnet, I learned to involve the people others do want to hang out with, and build from there.

If you’re hosting a conference, the obvious way is to begin with the speakers. Find an anchor and build around her. How do you get that first speaker? Try starting with a “two-fer” – find two speakers with a connection or friendship. If someone can combine a speaking engagement with seeing people they don’t often get to spend time with, they’re more likely to say yes. At Operator Summit, we invited fantastic speakers, but paired them each with a friend – like Eric Yuan with Jennifer Tejada, and Claire Hughes Johnson with Leyla Seka. This also applies when building a customer base: Garner a few respected companies/leaders as early adopters.

3) Be deliberate from the first engagement

You always have to make people feel comfortable – including those who don’t often join in. Last September, we put together Operator Summit in just 4 weeks. We knew we wanted a high percentage of women and people from underrepresented backgrounds, so we were public with that intention and deliberately reached out to people in those categories. It wasn’t a women’s conference or one for people of color, but we ended up with 80% women and 50% people of color.

This was another place being socially awkward helped. What would it take to get me to come to an event that’s full of people I didn’t know? A personal invitation, first of all – not a bulk mailing. Plus we asked those who were coming for names of contacts who might be interested, and then specifically mentioned the referring friend in that invitation. By the time you get to a SaaStr Annual size of 20,000 attendees, personal invitations aren’t always possible, but you can still do it selectively. The same goes for selling a product. Each interaction should feel personalized, so every prospect gets the sense that you are connecting with them as an individual and understand their needs.

4) Make it easy to participate

When you’re selling a product, you make it easy to buy. When you’re putting together a community, you make it easy to join. Start with scheduling. We have a lot of women with young kids in our Operator Collective community, so we try to schedule meetings and events at family-friendly times. Operator Summit, for example, started at 10 and ended at 4:30. When we have update calls, we try to schedule them for when we know people have finished dropping off kids at school, over lunch, or during a commute time. If we’re scheduling a group, we’ll often send a poll to ensure a critical mass.

The other key is to give people a role. It can be scary to walk into a new meeting or conference, so introverts like me prefer to have a task. At SaaStr Annual, “braindates” are wildly popular. At Operator Summit, we encourage people to sign up for our small group Office Hours.

5) Obsess over every detail

No matter what you’re building, you can never assume people will buy, join, or participate. You have to make it worthwhile, which means obsessing over every detail. What’s the mix of people, who will they meet, and what will make them come back? What kind of content will you provide and where will everyone find value? What’s the reg process, what about dietary restrictions, and what kind of swag? Obsess over every detail, from how they buy to how the product is delivered to the entire user experience.

Get Building

From the day we enter the working world and actually well before the need to network is hammered into us. We have to put ourselves out there and expand our connections in order to advance our careers. But communities can be a haven for the socially awkward: a place for people to find their niche and feel comfortable. And if this kid can grow up to be a super connector who builds successful network-dependent companies, I’m here to tell you that anyone can.

P.S. If you want to see my awkwardness in action, join me on March 11 at SaaStr Annual, where Leyla Seka, Lexi Reese, Elisa Steele, and I will do battle in an unscripted debate to determine the #1 secret to building high-performance orgs. I’m terrified already. 

How we brought so many first-time investors into venture

Why is the world of investing so insular? That was one of the questions we thought about as we created Operator Collective, our new venture fund designed to give talented operators from diverse backgrounds a safe, comfortable way to join venture. It was a good idea, right? A respectable pursuit?

Yet as we spoke to our wide networks of operators – most of whom happened to be women – there was notable trepidation. We saw it beneath their poker faces. These confident, ultra-talented operators with an absurd amount of collective experience building, growing, and running the world’s top enterprise companies were intimidated by the thought of investing in venture capital. Few had invested before, and if this experienced, savvy bunch shied away from the opportunity, how could we ever expect to bridge this gap?

It’s no secret that venture capital has long been an industry dominated by white males. As we’ve noted, this isn’t necessarily because no one wants a change, but rather because there hasn’t been a natural way for it to happen. And considering the gender pay equity gap and “gap table,” there never would be a natural way for this to happen unless we made one. If we want different companies, we need different venture capitalists We needed a new model. 

1) What if our LPs invested on a sliding scale?
So we started by creating a sliding scale to invest in our Operator Collective Fund. 90% of our LPs are women and 40% are people of color; because so many of them began their operator careers before the Equal Pay movement took hold, they’ve lost out on thousands (or even millions) of salary dollars comparable to others in their industries. A sliding scale for LP investments allows these experienced leaders to join the venture ecosystem at a level they’re comfortable with.

2) And they want more active roles
Even the sliding scale wasn’t enough, though. Beyond the financial side of the equation, our LPs wanted more. They didn’t just want to throw their hard-earned money at founders – there’s certainly no sure return on that investment. No, they wanted to help them build. Get hands-on, answer questions, serve as a resource. They wanted to share their experiences and lessons learned to advance the next generation. Refreshing, isn’t it? 

3) All while learning and sharing together
So now we’ve got our sliding scale and hands-on opportunities, but we still needed one more component to create the perfect trifecta for LPs. And it came from right within our own community: education. Operator Collective also has an education component designed to increase our business and investing acumen. Our own LPs lead webinars and host Office Hours. They meet 1:1. They offer up their expertise to anyone looking. It’s deliciously selfless. 

Our holy trifecta: Sliding scale, hands-on help, and education
What we’ve ended up with is a new model for venture investing, one that’s intentional and unique. By assembling these talented operators, offering education and experiential knowledge, and sourcing new opportunities together, we hope to #RiseTheTide in venture capital and create an industry where
everyone looks like an investor.

 

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

Why 90% of the Investors in This New Silicon Valley Venture Fund Are Women

FORTUNE MPW Next Gen 2019

This article by Michal Lev-Ram was originally published on Fortune.com.

On a recent Wednesday in Woodside, Calif., about a dozen Silicon Valley-based investors gathered to celebrate a new fund. These were some of the region’s top “operators”—the executives who make organizations tick day-to-day—from some of the hottest tech companies around, with many decades of experience (and financial success) represented in the room. But they also had something else in common: Nearly all of them were first-time investors.

Continue reading here.

Operator Collective is a diverse group of leaders working together to redistribute access to wealth, help more founders succeed, and disrupt the venture capital ecosystem. Learn more at www.operatorcollective.com or by connecting with us on Twitter and LinkedIn.

The outsiders are coming in: The origin of Operator Collective

For most of my life, I’ve felt like an outsider. Whether it was being raised by immigrant parents who didn’t understand Western social norms, or my years as an awkward kid picked last for everything, or being one of the few women Chief Intellectual Property Counsels in the niche-y field of patent law, I’ve always been most comfortable working quietly in the background.

When you’re an outsider, you spend a lot of time observing. I’m often told I think outside the box, to which I silently respond it’s because I’m not enough of an insider to even know what the confines of the box are. And when you’re an outsider, you sometimes don’t even realize you have skills that would be useful to others.

Here’s an example. In 2008 I helped launch a venture-backed company we took from $0 to $100M and IPO in three years but I was such an outsider to venture that I didn’t realize this was unusual. There were the inevitable and valuable lessons learned during that period, and we ultimately grew the company to $300M.

After we sold the company ten years later, I started to spend more time with founders and VCs, mostly as part of the SaaStr community, which I’d been involved in from the early days (I’m married to the founder). And of course, I spent a lot of time where I’m most comfortable quietly observing. Here’s what I saw:  

  • The venture world revolves around VCs and founders. 
  • Roughly 90% of VCs and founders are white males, higher when you look at enterprise.
  • VCs and founders tend to hang out with other VCs and founders, and their networks don’t overlap much with operators, much less with women operators. 
  • Most b2b startups eventually want to sell their products to enterprise.
  • The majority of VCs and founders have either never worked in enterprise, or haven’t done so in decades.  

As I began to dip my toe in angel investing, I noticed something else: I was often the only woman on the cap table, and homogeneous groups were showing up again and again. I was bothered enough to ask a few founders if they’d noticed. These founders, to their credit, were horrified, and then even more distressed when they realized they hadn’t recognized it prior to my asking the question. They explained that they’d simply gone to their buddies for backing they didn’t know any women who might invest and could I please help.

The Buddy Syndrome strikes again
The fact is, they weren’t wrong. When you’re in the early days of starting a company, you turn to people you know the ones who trust you and are willing to take a chance. And people from your network tend to be people like you. (I call this the buddy syndrome.)

And beyond this, it’s a fact that fewer women invest. Women hold 71% of their assets in cash. They make up just 9% of venture decision makers and 22% of angel investors. And if you focus only on my area enterprise the numbers drop even more.

At the same time, I began asking my women friends: “Why don’t you angel invest?” Never been asked. Never had the opportunity. Didn’t occur to me that it was a possibility. No time to vet and not sure I know how to vet anyway.

Why aren’t more women investing?
I heard this over and over and from some of the most accomplished operators in the world, many of whom happened to be women… leaders who’d built the most successful tech companies in the world. In fact, many of today’s most respected operators are women.

Earlier this year one of our LPs, Reshma Saujani, Founder & CEO of Girls Who Code, released her book Brave, Not Perfect; this is based on the idea that from a young age, boys are praised when they take risks, while girls are expected to be perfect and steer clear of taking chances. Saujani’s experience is in the world of coding, but the translation to enterprise is clear: Women today are conditioned to be perfect at work, at home, and frankly in everything we do. As a result, we give 150% to our day jobs and 150% to our family and friends. We’re not looking to meet VCs and founders in the little time we have left over. Sprinkle in the gender pay equity gap and “gap table,” and the result is that most women don’t have the liquidity, much less the desire, to invest in people they don’t know and in startups they don’t have the time to vet. Yet they’re the very people with the backgrounds the venture world could use. So these women these ultra talented operators were also outsiders with no obvious path to get in.

On the flip side, there’s venture. Now the value of diversity has been well established, yet venture remains homogeneous not because no one wants the change, but because there hasn’t been a natural way for it to happen (birds of a feather, and all that). So what we wanted to do was help both sides of the equation: Give talented operators from diverse backgrounds a safe, comfortable way to join venture + make it easy for founders and VCs to bring in new experience and perspectives.

The origin of Operator Collective
The idea took hold quickly. Operators were thrilled at the idea (just look at the absurd amount of talent we’ve assembled), and they quickly referred their fellow operators. Even universities and foundations signed on as LPs, a rarity for a first-time fund. And of course as we operators have been trained to do, we built this fund to have immediate product-market fit to address that gaping lack of operational expertise in venture.

So here we go. The sidelines are bursting, and the outsiders are coming in.

Say hello to Operator Collective.

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

Alpha Girls: 5 lessons from the women who earned their way to the top of Silicon Valley

Venture capital needs a hero right now, and it just might be the Alpha Girls. Alpha Girls is the story of four women whose hard work and dedication pushed them to the top of the venture capital world. It’s an undertold, yet necessary piece that details not only the rise of the title characters, but also of the venture and tech industries.

The four Alpha Girls — Magdalena Yesil, Sonja Perkins, Mary Jane Elmore, and Theresia Gouw — are an inspiration and a force for good, which is why we’re so proud that three of them have partnered with us at Operator Collective (and we’re working on that fourth). Here are five things I’ve already learned from Alpha Girls — and now that these women are on the OpCo team, I have a feeling these kinds of lessons are just beginning.

1) Emotional connections are incredibly important.

Venture capital has typically been ruled by white males — ambitious leaders with dominant personalities. As charismatic as they come across, they’re often lacking in emotional intelligence. Sonja Perkins filled that void with great success as a VC at Menlo Ventures. In the book, she talks about connecting with founders and forging relationships that lead to future deals. Presenting to a room full of experienced VC can be incredibly intimidating for a founder; Sonja’s easy-going demeanor and outgoing personality helped to put them at ease, leading to smoother presentations and more investments.

2) It’s OK to make the first move.

There’s an old philosophy that women shouldn’t make the first move, but that kind of thinking is laughably antiquated. Like many industries, venture capital is all about timing, connections, and the flow of information, so waiting to make a move only opens the door for the next person to come in and take it. Theresia Gouw’s quick moves helped her firm land several deals, including Facebook, while Magdalena Yesil’s foresight and connections helped her become the first investor in Salesforce (for which I am very thankful!). These successes and others are largely dependent on the Alpha Girls’ abilities to think and act quickly.

3) You never know when or where a connection will resurface.

Connections are important in any industry, but in venture, they’re vital. You never know when an old acquaintance or former colleague might resurface, opening the possibility of a deal. Magdalena Yesil recounts the story of confronting Larry Ellison at the gym, of all places. MJ Elmore and Sonja Perkins discuss how their networks and connections lead to major new deals. And what a strange connection that Theresia worked with Timothy McVeigh at a Burger King in high school. It’s a small world after all, or so the song goes.

4) Find people who support you at work and at home.

It’s always important to find your people — the ones who support and challenge you, and the ones who’ll have difficult conversations with you when needed. Theresia Gouw was at her desk one day when fellow VC Jim Goetz came in to let her know about rumors circulating that she was sleeping her way into deals. Rumors like these were nothing new to her, so she blew them off — but how great to know Jim had her back. At the other end of the spectrum, MJ Elmore realized after many years that her marriage wasn’t an equal partnership. Her husband had been supportive of her career and they worked equally hard, yet MJ was the one handling all the household responsibilities. Eventually the imbalance lead to divorce; today MJ advises women to discuss things like this early on with their partners to establish expectations.

5) Pick your battles when it comes to sexism.

The feminist movement has shined a light on equality and is doing wonders for women around the world. More and more women are rightfully calling out sexism when they see it. But at the same time, as the Alpha Girls demonstrate, you’ve got to choose your battles. Theresia Gouw recalls stories when founders asked her to get coffee, assuming she was in the meeting to take notes. Sonja Perkins shares a time when she lived in a pool house for free, but was expected to babysit the homeowner’s triplets. Both women could have made a stink about gender norms, but chose not to: Theresia said the embarrassment these men felt when they realized their mistake was palpable, and Sonja didn’t mind the work exchange. Sexism is rampant, they said, but there’s no need to go looking for it.

Alpha Girls and Operator Collective

Alpha Girls offers a fascinating window into Silicon Valley as the four title women use their grit and intelligence to succeed in an industry that’s heavily dominated by men. Given their intimate experience in venture, the Alpha Girls are an incredible asset to the Operator Collective team as we work to diversify the industry, break down the barriers to entry, and encourage wealth redistribution. This book is a treasure trove of stories and inspiration, and I can’t wait to see what’s ahead for these four women — at Operator Collective and beyond.

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

Learning From Operators: SaaStr Co-founder Mallun Yen’s Next Venture

This article by Gené Teare was originally published on Crunchbase News.

Mallun Yen’s latest endeavor, Operator Collective, launched its first summit bringing together operators of high growth venture backed companies.

As a writer focused on female founders and executives, I was invited to cover the event. Yen noticed that the venture world tends to revolve around founders and VCs. Yet her experience as an early team member at RPX and a co-founder at SaaStr is that COOs and operators are critical but do not spend time connecting.

Continue reading here.

Operator Collective is a diverse group of leaders working together to redistribute access to wealth, help more founders succeed, and disrupt the venture capital ecosystem. Learn more at www.operatorcollective.com or by connecting with us on Twitter and LinkedIn.

Finding Empowerment in Community: Lessons from the Operator Summit

This article by Jen Yip was originally published on Medium.

Yesterday I had the privilege of attending the first-ever Operator Summit organized by the inimitable operator extraordinaire, Mallun Yen, co-founder of SaaStr and founder of the Operator Collective. I left the event just as the sun was setting, reluctantly pulling myself away from a group of women still laughing together on the sidewalk, feeling more energized and inspired than I can remember having been in a long time. As someone who hosts and attends many tech events, I can say this feeling of kinship with fellow conference attendees is pretty rare. I hardly ever leave an event with this heady feeling of empowerment. This morning on my run, I spent some time reflecting on what made the Operator Summit so powerful.

Continue reading here.

Operator Collective is a diverse group of leaders working together to redistribute access to wealth, help more founders succeed, and disrupt the venture capital ecosystem. Learn more at www.operatorcollective.com or by connecting with us on Twitter and LinkedIn.