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Entrepreneurship

When I started at Hotmail in 1996, we were thirteen people, and frankly, we didn’t know what we were doing… The company had recently launched the first Software as a Service (SaaS) application to the world, and we were struggling to keep it up and running.

Everything about it was just so different than the traditional software we were used to:

  • We had one version of the software that was being used 24/7, as opposed to 5-10 versions.
  • We rolled out new versions every few weeks, versus months or years.
  • The end users were part of the quality assurance process and we were in a constant state of rolling new bug fixes, as opposed to a huge QA staff and a long process.
  • The software engineers had to learn to collaborate across functions with the data center techs, who rolled out the code, and the customer service group that was getting the customer QA data — compared to before, when those organizations were siloed.
  • We could see exactly how the end users used the software — real time — which dramatically increased the innovation cycle. This was very different from past approaches, where you had to do focus groups to figure out how an end user was using the software.

These were major shifts, and we weren’t sure how to organize for success … but somehow, we muddled through it.

As it turns out, though, we weren’t the only ones — just about everyone involved in the early internet era who had come from traditional, waterfall-centric programming environments started inventing new ways of doing things that were more in keeping with the always-on, fast-release iterative cycle that especially suited the world of the nascent SaaS and web-based software environments.

In 2001, a group of developers met to debate and discuss a new set of “lightweight” methods for software development, and the Agile Manifesto was born. While the manifesto wasn’t necessarily a direct outcome of the new web/SaaS/cloud organizational meanderings, it struck a nerve by stressing the need for cross-functional collaboration, communications, and short release cycles. Essentially, it helped to codify the hodgepodge of learnings we independently discovered about what worked at Hotmail, Yahoo, and other first-generation internet companies. These learnings ultimately became the underpinnings for what we now call “DevOps” [adapted from Wikipedia]:

DevOps (a portmanteau of “development” and “operations”) is a software development method that stresses communication, collaboration, and integration between software developers and information technology (IT) professionals. A response to the interdependence of software development and IT operations, DevOps aims to help organizations rapidly produce software products and services — and to improve operations performance.

But DevOps is more than just a methodology. It’s a must-have skill set for the modern programmer — and is increasingly becoming its own department as well (the subject of much debate). The rise of the hyperscale cloud datacenter has made this job much harder as developers have had to hack together tools and complex scripts for pushing code to thousands of pancake servers.

The growth of the DevOps movement coupled with this complex cloud infrastructure has opened up an opportunity for a company to own the entire process and help developers and managers manage it.

It is with this backdrop that I am pleased to announce Andreessen Horowitz is leading a $2.8M Series A in Distelli, an infrastructure automation company that I like to think of as the “DevOps dashboard.” Here’s why we’re so excited about the company:

  • It was founded by Rahul Singh, one of the early engineers on the Amazon Web Services team. Rahul is the epitome of one of our most important criteria — founder/market fit. He has essentially solved a set of problems he encountered during his nine years working on Amazon’s cloud.
  • Rahul has a grand vision for Distelli to become the DevOps platform. Application, database, and middleware deployment are just the first tasks that Distelli automates, and they’ve got a rich roadmap to automate the other things DevOps does.
  • Shortly after the first beta, the product was of such high quality that every proof of concept resulted in a paying customer. The customer references raved about how it was simple, scalable, and consistent across multiple cloud and on-premise installations.
  • When it seems like every smart entrepreneur we meet seems to adopt the same new technology at once — indirectly demonstrating it as part of their pitch — we pay attention. A few of the companies in our portfolio that hold this important distinction include Good Data, Mixpanel, Okta, Optimizely, and Zenefits; and now, Distelli.

Rahul is one of those “10x founders” (as we like to call it) that just get shit done at an astounding rate. (These are the founders to whom you’re about to share feedback you’ve heard or suggest a new feature and they’re like, yeah, we already did it.) Every month I check in with Rahul, it feels like he’s progressed ten times more…

I’m so pumped to be joining the board to help Rahul grow into a powerhouse, and am pleased that Distelli is joining the a16z family. Onward!

One of the rookie mistakes first-time entrepreneurs often make is to be too guarded about their idea – in fact, many will actually spend their first $25,000 on patent lawyers without ever fully vetting their product. In order to gain credibility and attract investor attention, it’s critical to aggressively seek out the most relevant people in the world and get their feedback. I believe most young entrepreneurs massively overestimate the chances of someone stealing their idea versus the benefits associated with sharing it.

When my co-founder and I first had the idea for IronPort, an email security company, we triangulated a list of the 20 most relevant people in email – former CEOs, open source technologists, investors and thought leaders. After we had the target list, we got resourceful in getting to them – friends of friends, cold emails and FedExed letters. One of the tactics we used was trying to get a diagram of our technology into their hands — subject matter experts just couldn’t resist correcting our analysis. Here are the huge benefits with taking the “sharing” risk:

Fix your compass. The experts can immediately get into the weeds and help steer you around the potholes they went through and make sure you’re not headed for a cul-de-sac. The input we received proved essential to refining our idea and setting our order of battle. We gave a number of these experts equity grants to become formal advisors to the company.

First employees. Two of the people on our list became employees after we went through the idea with them. One had built PayPal’s email infrastructure and the other had built Newman, the massively scalable eGroups email engine. The experts typically know where the other best-in-the-world talents are currently working and can help you recruit them in with a credible intro.

Investors. Our friends and family seed round became a who’s who of people who had done interesting things in email. The PayPal founders, the eGroups founders and the Hotmail founders all ended up investing. You can imagine the warm VC intros we received from a massively credible angel investor right in their subject area strike zone. In fact, on more than one occasion, a VC would say, “I’d like for you to meet with so-and-so to better understand the technology.” I would reply, “Oh, so-and-so? They are already an advisor/investor…”

It’s really hard to break through the clutter and get the attention of the top investors as they typically only look at deals that come in from a warm, credible referral. There’s absolutely nothing more credible than getting an endorsement from a well-known subject matter expert who has already put their own money into your company.

This post originally appeared in the Wall Street Journal.

In many of the old war movies, every elite unit has at least one member that has the critical talent to make something out of nothing: the scrounge. You know this guy: when everyone is out of rations or ammunition and the truck is broken down, he quietly heads out. The next day, when all hope of completing the mission seems lost, the scrounge comes rolling up in a freshly repainted jeep, full rations, ammo, and, stereotypically, a case of cold beer. How did he do that? Where did it all come from? “Don’t ask,” he growls, “Let’s get movin’.”

Harvey Keitel’s Winston “The Wolf” Wolfe in Pulp Fiction is another iconic fix-it guy. He comes directly from a party in his tux to “clean up” the situation. I love his “Can I get some coffee?” calm demeanor as he carefully assesses the situation, starts prioritizing, and then takes swift action to get Jules and Vincent out of their blood-soaked jam.

During a crux scene in Apollo 13, the engineers in Houston realize they have to somehow fit the Command Module’s square carbon dioxide filter in the Lunar Module’s round receptacles if they want everyone to keep breathing. They got together in a room, dumped the box of materials available to the astronauts on the table and said, “Here’s what we have to work with…” After working for a tense few hours, they cobbled together a solution with step-by-step instructions for the oxygen-starved astronauts. That scene always gives me goose bumps.

All of the successful entrepreneurs I know are part-scrounge, part-Wolf, with a good dose of calm-under-pressure space jockey thrown in. In other words, they are ridiculously resourceful. It’s this magical combination of wicked-smart, tenacious as hell, works harder and longer than most people think is humanly possible, thinks way outside the box and is also unbelievably passionate and compelling. In short, they have special tools to just get shit done.

Special, but not unobtainable.

Over the years, I’ve noticed some patterns and methods that explain how great people manage to pull off the impossible. And with Mr. Wolfe’s permission, here they are:

“Crack the egg with a sledgehammer.” This was a quote from my VP of Engineering, Nawaf Bitar, at IronPort. When IronPort anti-spam wasn’t working and it looked like our partner Brightmail was going to terminate our contract, we had a complete “Oh shit!” moment. Nawaf moved the entire engineering team over to work on it. He called them all in to work nights and weekends until it was fixed, and urgently sought out every anti-spam expert on the planet to help or to hire. Other people would have done one or two of those things – he did them all simultaneously and immediately. Nawaf saved our bacon.

Set a measurable goal and brainstorm like hell. When we were developing our first product at IronPort, we desperately needed to get feedback from email administrators at large companies. Our dream was to quickly talk to 50 of them to get to a critical mass, but how the hell do you do that when you don’t know any? We brainstormed, tested, stalked, and leaned on our networks. We made a list of the Fortune 500 and tried to line up anyone we knew on the inside. We all went through our school alumni networks.

“Can you introduce me to someone who runs your email? Who do you call when email goes sideways?” Everyone we did get through to was pumped for information to get to more: “What conferences do you go to? What do you read? Who else can you introduce us to?” We reached 43 of the exact right people — not quite 50, but it did the trick.

Cheat time. During a board meeting last year, Quirky’s CEO Ben Kaufman recounted a story about preparing for a critical Home Depot meeting. Quirky was just starting to build things for the “connected home” and Home Depot was a dream opportunity. When he got the call in New York one afternoon that the home improvement giant could squeeze him into a new product-review meeting the very next day in Atlanta, he brought nearly the whole company in for an all-night prep session. They split up into five different teams and came up with seven working products — overnight. They packed up prototypes of a Wi-Fi-enabled mousetrap, garage opener, smoke detector and water sensor, among others, and then slept on the flight down. A month later, Home Depot ordered $7 million worth of products.

“Insanely violent passion.” This is a phrase that I’ve heard used to describe Andrew Rubin, the CEO of Illumio. Andrew came out to Silicon Valley from the Midwest with virtually no connections. Within 18 months he raised two rounds of capital and hired one of the best leadership teams I’ve ever seen. How did he do it? Andrew “glows in the dark.” He is so charismatic, compelling, logical, and excited about what he is pursing that you can just feel the energy — even see it glow. Getting to the right person often requires a series of small baton passes or jumping from lily pads of different people to get to your destination.

Andrew was unrelenting  when it came to asking for suggestions and pursuing connections and introductions from just about everyone. And since he came across so passionate and compelling, people actually felt like they were building social capital by helping him.

Foot squarely on the line. I wouldn’t suggest that being resourceful has anything to do with doing something illegal or unethical, but I’ve definitely noticed a pattern of being “creative.” When my then head of sales, Shrey Bhatia, was trying to close a $900,000 purchase order from DoubleClick in New York, he called up the CIO and said, “Hey, I’ll be in New York tomorrow, could I drop by for 15 minutes to discuss this?” Of course, he had no intention of going to New York unless the CIO confirmed the meeting. When the CIO finally did, at around 7 p.m., Shrey turned his car around, jumped on the red-eye, slept on the plane and brought home the order the next day. We had the check framed.

Pulp Fiction’s Winston Wolfe is obviously a fictional character, but the stereotype he represents is worth exploring. A guy that’s seen it all, he’s completely unflappable, methodical and decisive. How did he get that way? Like an old sea captain, he is the sum of so many hard-earned life experiences of living on the edge.

While there’s no substitute for real experience, I believe it helps to hear and share stories of resourcefulness in action — almost like case studies in school. With every new account, we open our mind to a new path to take and learn the tactics that others have used to overcome much larger obstacles than the ones that are currently in front of us. I’d love to hear about more “great moments in resourcefulness” in the comments section.

This post originally appeared in TechCrunch

“There was never any trust there. He was constantly conspiring behind my back with the other board members. At the board meetings, it was clear that he was leading a bunch of side conversations…”

I heard this quote from a CEO I had called for a backdoor reference on a potential board member for IronPort. It instantly made me realize the importance of transparency between a CEO and his board. If I were to totally suck at being a CEO, I wanted someone who would have the hard conversation with me. How else does someone learn and improve?

As a first time CEO, I wasn’t sure if I would scale to run IronPort long-term. But I wanted a legitimate shot at it. And I wanted a board member that considered the company’s interest first, but was also committed to helping me become a better CEO.

I will never forget that backdoor reference because it made me think twice about the fundamental skills and characteristics I wanted in a board member. Early on it became clear that transparency and the ability to provide honest feedback were paramount. I learned this through receiving instant and honest feedback following every board meeting (a healthy board practice). When this was coupled with annual 360 performance evaluations I always knew where I stood. The feedback was crucial for my growth.

In addition to transparency and feedback, through my own personal CEO journey, I came to realize that the following represents table stakes for the best board members:

Experience: I wanted someone that had been there, done that. In addition to the investors, I went out of my way to recruit three CEOs to the IronPort board because I wanted to surround myself with people that could help steer me around common potholes and would be unflappable as things were going haywire. Diversity of experience was also very helpful. Some of my board members had been on 50 boards while others had run large direct sales organizations; both contributed in completely different ways. If given a choice, I don’t see why any entrepreneur would take a term sheet from a VC with little or no board or operating experience.

Sharp opinion: Quiet is not helpful. A Melvin Milquetoast who sits there nodding his head all meeting is not helpful. I wanted someone who consistently contributed meaningfully and constructively to the conversation, however wide ranging it became. Every board member slot is an opportunity to find someone truly amazing who will speak up and help you build your business. The traditional “financial expert” as a board member essentially compromises a valuable seat with a former CFO or accountant that rarely contributes outside of their domain. It’s worth working hard to find a CFO that later became a CEO or interviewing hard for a financial expert who really contributes. The thorniest business problems will surface at the board meetings and the different, sharp, opinions help to to better explore the poles of the arguments to make better decisions.

Responsive: Board members need to respond to texts within hours and emails or phone calls within 24 hours – no excuses. Things move fast at startups and when I needed help with a lawsuit, contract, employee situation or financing, I wanted to have a damn batphone with my board members. Yes, I realize that I was not in the business of saving lives, but the difference between landing a rock star candidate or closing a round often depended on the timeliness of a board member’s response.

Does real shit: Being on a board is not just about showing up for the meetings. A board member needs to materially contribute to the success of the business. This includes making numerous introductions to potential customers, partners and employee candidates. This is in addition to being available to interview/sell employee candidates, coach management team members, speak at sales kickoffs or just about anything reasonable that a CEO asks you to do to help the business.

I once had a venture capitalist explain to me that a board doesn’t have many options when it comes to affecting the direction of the company. That if you don’t agree with where the CEO is leading the company, you basically have two levers: 1) threaten to fire the CEO, or 2) fire the CEO. He also added that the former gets pulled much more often than the latter. This describes well the authoritarian and adversarial nature of many CEO-to-board relationships. Given the makeup of most boards, where most of the members lack the practical experience to help coach the CEO, the lever approach is not all that surprising. But like any bad relationship, it’s something to avoid.

The best board members aren’t elected by default. CEO’s that set themselves up with their choice of board member – which means getting more than one term sheet and doing extensive reference checking – are better off. You want to find a coach, not a lever puller.

There is a perfect storm of three distinct disruptive forces that has the potential to topple nearly every major enterprise software incumbent. And the traditional approach of dealing with technology shifts – through acquisition – looks like it’s headed towards failure. As such, there is an unprecedented opportunity to create many, new multi-billion dollar enterprise franchises that are on the right side of these forces and are willing to go the distance in the face of ridiculously high acquisition offers.

Let’s examine these forces individually:

Software as a service (Saas): Seemingly a little long in the tooth as a disruptor, Saas has finally gone mainstream in the Global 2000. The primary disruptive force of this technology is the speed of innovation. The feedback loop is especially powerful: as opposed to using focus groups and surveys to figure out how users are interacting with the product, Saas companies can see what their customers are doing real-time by capturing and analyzing every click. They quickly extend their products through a “cell division” that continuously builds out and A/B tests the features that are getting the most engagement. On-premise and client (PC) software-based product cycles can’t possibly compete here as new releases are typically pushed 10 times faster at 45-60 days vs 18-24 months. There’s always one version/code base so it’s much easier to support, patch bugs, and roll out new features to all customers at once. The old joke of “How did God create the world in 7 days? He didn’t have an installed base!” certainly applies – but Saas also demands entirely new skills sets associated with running a 24×7 services business. Dev/Ops, customer care centers, network operations and delivering uptime via failover, mirroring and hot backups are all new and essential. It’s easy to see how the early Saas pioneers gained so much ground with this innovation but even they are unprepared and poorly architected to take advantage of the additional disruptors that have hit more recently…

Cloud infrastructure: As I detailed in a prior post, “The Building is the New Server,” the humongous internet powers, Facebook and Google, are literally breaking new ground in re-imagining the design, components and cost of running a hyper-scale data center. The cloud infrastructure they are pioneering has the primary disruptive force of massively driving down cost. Facebook, for instance, is experimenting on the bleeding edge of solving the new cost bottlenecks of power and cooling. I recently read that it actually rained inside one of their datacenters. The cloud service providers (CSPs) are following their lead using commodity components, open source software, data center design and testing software defined storage and networking products to enjoy the same, devastating cost curve. The corporate datacenters (aka “private clouds”) will slowly disappear as Global 2000 companies migrate to these irresistible new cost curves. Don’t be fooled that security and reliability concerns will keep large enterprises away – as the CEO of IronPort, I watched in horror as large enterprises started pointing their treasured Mail Exchange (MX) records to cloud services like Postini – a much superior and vastly cheaper cloud based architecture versus our perimeter appliances. And email is the most sensitive and mission critical of applications…

Mobile: About two years ago, all of our consumer companies went through an “Oh shit!” moment with mobile. One year mobile was 10% of traffic and the next year, when everyone was expecting ~20%, it was 30% on it’s way to 50%. Facebook, for instance, famously bought Instagram for $1B and then continued their pursuit of talent to redesign for mobile. The new mobile operating systems and devices are proliferating an entirely new interaction and design paradigm that has the primary disruptive force of a re-imagined user interface. The innovative use of touch/gestures (e.g. pull down, swipe, pinch etc.) pioneered by the consumer applications will become de rigor for enterprise as well. Although it’s still early, the mobile sensors (e.g. GPS, accelerometer, video etc.) will also become integral and spawn new innovations in the enterprise as they have enabled new consumer franchises like Lyft and Instagram. The number one problem facing so many of the startups I talk to is hiring the design talent (e.g. Mobile app, front-end engineering and user interface) to take advantage of this trend. In addition to being in ridiculously high demand, most of these people are “arteests” who eschew just cash and stock as incentives because they want to work for a purpose and in an environment where design is an overarching priority/core competency – not something that is grafted on afterwards. These environments are hard to find.

So exactly why won’t these big incumbents make it to the other side? There are just too many things changing at once. Beyond the technology changes, there are structural impediments as well. The incumbent sales forces have become farmers instead of hunters. They still sell on relationships (e.g. A round of golf, anyone?) and bundling/discounting instead of product attributes. They sell to the CIO instead of the line of business buyer who is making the decision. The quotas and incentives are too different. The accounting systems don’t speak recurring billing and revenue. Ugh – it’s just too much change…

A handful of exits have been priced based on a NTM revenue average of 11X vs around 4X for the rest of Saas companies. Examples include Workday, Splunk, ServiceNow, Marketo and Tableau. Not to mention the SuccessFactors deal (done at 11X) has officially kicked off the next wave of consolidation. On the private side, companies like New Relic, AppDynamics and ZenDesk have seen private transaction multiples of between 9X and 11X.

There is outright panic going on right now at the large incumbents as they pay ridiculous premiums for the early Saas companies. And so why won’t these acquisitions pan out? Most of the early Saas companies weren’t architected to take advantage of the cloud infrastructure cost advantages AND most completely missed the boat on mobile. It’s hard enough for new, cool enterprise startups to hire the necessary design talent but the large incumbents really have no hope.

Next Up

As I’ve said, there is a perfect storm of three distinct disruptive forces brewing which has the potential to erupt into a new multi-billion dollar wave of enterprise franchises. In particular, there will be at least 30 new enterprise franchises that will go the distance, resist high acquisition offers as they either supply or ride this trio of disruptors to dominance.

Amongst others, the new suppliers are companies like Cumulus Networks, Okta, New Relic and Nimble Storage. The “riders” are awesome trifecta companies like Box, Evernote, Base, Expensify and Tidemark.

Where will these 30 New Franchises come from? A double investment cycle in Saas, as the large incumbents buy the early Saas pioneers and fumble them, will pave the way. Like Lenny from “Of Mice and Men,” they will smother these companies with too much negative attention, mismatched salesforces, and misunderstood business models. Following a short vesting period, the product and management talent – who are used to working at a completely different pace – will ultimately leave the incumbent, resulting in a bevy of entrepreneurs that roll out to start even more of these franchises.

I can’t wait to meet them!

🙂

All great pitches have a few things in common: the founder/team is wicked smart, the idea is big and a breakthrough, and the market is potentially enormous.

But the best pitches are also usually non-obvious and unique to the particular entrepreneur’s story and background. “Founder/market fit” is important. Does the founder’s life story, educational background, personal struggles, Ph.D thesis, or prior work experience somehow qualify them to unfairly prosecute the opportunity they are pursuing? At our firm we always start off our meetings with a deep dive into the entrepreneur’s background, and the most convincing pitches literally pour out of them with some deep connection or “aha” that led them into the business they are explaining. By doing so, the idea is unique/original and is presented authentically versus a canned sales presentation.

A lack of originality and authenticity is probably the biggest turnoff. Stereotypically, this can be a couple of MBAs that have been churning through different business ideas in order to find something that might make them rich. Or it could be a hired gun/former sales VP as the CEO adopting or explaining someone else’s idea. In both cases, they typically have done a superficial, McKinsey-esque market analysis but have no passion or connection to the business.

Another important quality of a “perfect” pitch is when a founder exudes in many different ways, the confidence and courage to go the distance, against improbable odds, to make an enduring or lasting business. They come off as expertly informed, determined and unflappable during the hard questions. And they usually lay out a series of chess moves that reveal an even bigger ambition: “If we do this, then we can do that…”

A lack of confidence is also a huge turnoff – usually typified by a single slide in the deck entitled, “Exit Strategy or Exit Options.” This is the kiss of death for our firm.

This post originally appeared on the WSJ Accelerators Blog.

It took almost six months for my former company IronPort’s acquisition by Cisco to close and it seemed like forever. Although I was still the CEO by name, I was essentially running a “puppet” government with every hire, major expense and strategic shift needing explicit approval from my soon-to-be-overlords. Since Cisco was a functionally organized company, I would soon be losing half of my direct reports as sales, HR, and finance would report into their respective groups. My job was becoming smaller and it had considerably fewer degrees of freedom. So here was the big dilemma: I had signed up for 24 months of re-vesting my founder’s shares that wouldn’t begin until the deal was closed and it already seemed like a paint-drying eternity. I was pretty sure that I wasn’t cut out for a big company but I just couldn’t spend the next two years watching the clock or I’d spiral into insanity. What to do?

An analogy hit me as I watched my son at recent team practice: Water polo. Despite growing up on Florida beaches, I’m not that great of a swimmer. I’ve never even put on a Speedo. I didn’t think that I would like anything about water polo. However, if I was locked in a sports complex every day for two years and everyone else was playing water polo — how long could I sit on the edge of the pool before I gave it a go? Should I just go through the motions? Splash water on my face and feign participation? No, I came to believe there was only one way forward: shave all the hair off my body, put on the Speedo, start throwing elbows, making shots and playing with vigor…

Seriously and specifically, after six months in, I strongly advocated to be put in charge of all Security products at Cisco — a business that was three times larger than IronPort. I believe if the leaders of a newly acquired company are locked up for a significant period of time (>18 months), they should strongly advocate for bigger jobs within the acquiring company. This is especially true if the leader isn’t planning on staying around after the vesting period. This may seem like odd advice, but here’s the rationale:

It’s not about you, it’s about your team. If you’re a disaffected leader, moping around, “doing time” and talking smack, your team will disintegrate and the acquisition will fail. On the other hand, if you land a larger role, you are in a unique position to help them out. You owe it to the people who ate Ramen noodles while you paid them in potentially worthless stock to work at your company in the beginning. In addition to promoting some of them to larger roles within your new org, you will be much more connected to the cross-company opportunities and can advocate for your top performers. When your team sees you engaging, they are more likely to pull harder, too. Most of the mid-level managers at IronPort had a significant increase in their responsibilities at Cisco and it prepared them to take on even larger roles both in and outside the company. There is a myth that employees that come from a startup aren’t cut out for large companies — in fact, many may be ready for a change. Over the eight years we built IronPort, many of our single employees got married, had kids and wanted the current income, benefits, lighter work hours, and increased stability of a larger company.

You need to “sew in the organ” to make the acquisition successful. Most acquisitions fail. If something isn’t big enough to stand on it’s own or doesn’t logically snap into an existing business line, it will usually wither and die. This is especially true if the acquired leaders leave or become disaffected. Employees mimic leaders’ behavior or get shifted to new leaders when the previous ones exit and have no connection or trust with their new reporting chain. If the leaders take larger and different roles within the acquiring company they form beachheads of trust and points of navigation. It becomes less “them” vs. “us” and a more collective “we.” Look, I’m not saying it’s ever going to be Kumbaya over s’mores, but it’s a helluva lot easier to accept the bullshit you get at a large company if you have someone you trust explaining the rationale to you.

You will meet amazing great people as you get closer to the inner circle. If your head isn’t in the game, you’ll never spend any meaningful time with the best people. After my promotion, I got to spend a ton of time with the senior team, went through their version of VP leadership training, and tackled many tough strategic issues. I believe it’s only by really getting to know the key people that you can make an informed decision about making a career at the new company. Yes, I met my share of climbers, passive-aggressive assholes, and C-players but that didn’t really matter long term. The rockstars I came across have become lifelong colleagues — some of whom have stayed — but many have moved on to bigger, more interesting jobs in hot Silicon Valley companies. Don’t overlook the importance of this opportunity.

If you decided to take my advice and push for a larger role, I have a few more suggestions once you’re there:

Don’t play favorites with your old team. If you’ve run a successful startup, you’ve likely attracted first-rate talent to join you. Invariably, the close relationships, trust from working together, and familiarity with their great work will lead you to promote them first and fast. However, it’s important for them to earn some credibility with the new organization first. In retrospect, I moved too quickly and put my old team in charge too fast. We suffered from a perception of an “IronPort takeover” that was hard to reverse. I should have taken more time to evaluate my inherited Cisco team and let the cream of the crop rise naturally.

Mix up the talent. When we announced the reorg, I shuffled the leadership decks completely. The IronPort SVP of Engineering took over the firewall group and the Cisco VP running firewalls took over IronPort. Each had a fresh set of eyes and legs to apply to their new areas and attacked getting up to speed with vigor. In addition, we flew in all the director-level leaders and above from all the product groups to do group brainstorming and come up with new roadmaps for every product. Because the plans were argued and debated out in the open with everyone involved, there was much more buy-in with the employees working on the products.

Speak your mind. I was constantly pointing out inconsistencies, stupid directives, red tape, and anything that got in the way of doing the right thing. The fact that I wasn’t nursing a 10-year career trajectory and was on the fence about staying long term was incredibly freeing in terms of getting things done. In general, large companies get caught up in their processes so much that the leaders forget how to push to do the right thing. In addition to making the experience more entertaining, I met a bunch of other, like-minded leaders and made progress on important projects.

Negotiate for more compensation. Although this is starting to change at companies like Facebook and Google, most large companies are not prepared to be competitive with hot startups for compensating executives. As the leader, you can create a business case of what a comparable compensation plan would look like for a CEO of a private company. The main benefit here, again, is for your team versus you. If you can set up a compensation umbrella for you, it will apply directly to the rest of your executive team and top engineers.

Put together a succession plan. (Especially, if you’ve definitively decided it’s not for you.) In today’s world, 18-month stints are the norm at well-run large companies so there’s no need to feel bad leaving at the end of your vesting period. If you’ve integrated the team, someone would have likely distinguished his or herself and can be promoted into your role. If you’ve addressed your compensation and met all the best people, you’ll have all the data in place to make an informed decision to stay or move on.

In the end, for a variety of reasons, I left Cisco two years to the day when my vesting period was over. My former SVP of marketing at IronPort took over my role as head of all security products at Cisco. Many of the best people at IronPort stayed at Cisco for many years after their IronPort vesting was over. I believe the main reason the acquisition was a success was because the team engaged and meaningfully integrated into Cisco.