Category: Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup

Going From Enterprise Sales Manager To Startup VP of Sales? Velocity And Focus Are Your New Normal

Going From Enterprise Sales Manager To Startup VP of Sales? Velocity And Focus Are Your New Normal

The next in our series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup” where we discuss your promotion from individual contributor to leading a team. Is it for the faint of heart?

Navigating the move from enterprise executive to startup VP of Sales or Chief Revenue Officer is not for the faint of heart. However, for successful managers, the disruptive nature of startups can be cathartic.

You are probably a lot like me. You went from an individual contributor or a front-line sales manager for a big company with lots of resources to a team lead at a small company with limited resources. A sales manager at a major corporation and an executive at a startup may seem like they have more differences than similarities, but experience in the former helps inform the latter.

For executives considering doing this move (or if you have already made the jump), this move is wide open with opportunity. Here’s how to take advantage of it.

Know Your ‘Why’

The grass is not always greener. Startups are not a reprieve from corporate life; they live on the razor’s edge of “scale or die.” Time and mediocrity are enemies. Startups typically move fast to create solutions that can scale across industries and sectors.

In this environment, it’s important to have a “why.” The “why” is different for every executive — and truthfully, it can be quite personal. Some questions executives may want to ask themselves while considering the move include:

  • Do I want to build solutions to problems I’ve encountered throughout my career?
  • Do I want to get back to creating?

For example, our customers get the benefit of Kubernetes. According to Gartner, containers and using Kubernetes to orchestrate containers is the de facto choice for the next generation of software infrastructure. When I saw the reference architecture for Agile Stacks, I knew we had a game-changer that enterprise buyers need because every company on the digital transformation journey must build software better and faster. And the velocity, matched with a rigorous focus, is what I need at this stage of my career.

Find Your ‘Who’

I was introduced to my current startup by one of their Board members that I have known for years. When I met the CEO, I found that we shared similar industry observations, and I found myself excited about his market vision, company, and approach.

If you are joining an existing founder, you have a lot of research that you must do and it won’t be as easy as joining a big company with a lot of documentation. Research the company beyond financials, business model, product, and technology. Understand the startup’s culture; invest time and effort into exploring whether the executive-partner relationship can build a foundation for mutual success.

Assess Your Industry Expertise

Soon after talking to the company, I realized my new company had built actual solutions for some of the problems I had on the enterprise side. I could leverage my industry expertise to help the company execute its product vision, accelerate time to market and deliver quality solutions. When I considered leaving a global enterprise for a startup, it had to be the right one.

Startups should meet or beat milestones, and the industry expertise of their leaders can be a driving force to provide rigor. Executives must self-assess how deep and how broad their industry knowledge is. Do you fully understand the ecosystem and how you can help a startup impact, and potentially lead, that industry? Can you bring market vision, build strategic partnerships, drive maturation in existing products, expand the book of business, develop talent, deepen customer relationships, or create operational efficiencies to enable faster growth?

Fight Through Ambiguity

There is no room in a startup for executives who are unwilling or unable to be operational and visionary. It is not possible to understate the level of foresight, flexibility, and agility required in this environment.

You must continuously recalibrate your approach to operational efficiency, as working with limited resources forces me to ensure I am creating value at every turn.

Create Value

Within many large companies, the Silicon Valley mantra of “move fast and break things” doesn’t necessarily translate. Large companies have the resources, money and institutional support unavailable to start-ups, but they rarely have the focus to solve industry-sized problems. And they must measure and manage risk daily.

Further, while startups are relatively flat, large corporations are highly matrixed. In order to be a successful sales executive, it’s imperative to build relationships across departments. People need to trust that moving forward will benefit them.

Any executive joining a startup should focus on the value they create as an individual. What do you bring, above and beyond the job for which you were hired? Ask yourself if you have the emotional quotient (EQ), for example, to serve as a translator to the enterprise on how to evaluate product fit while coaching a startup team on how best to work within enterprise processes for implementation. That’s creating value for both sides.

Get Accustomed To The New Normal

Velocity and focus are my new normal. You must create more with less, fast and with laser-focus on impact. Startups can accomplish more in weeks than a large company could do in years, if at all. However, that rapid advancement can easily cause the company to go into disarray. It is simply not enough to have velocity, you need to have velocity towards your goals as a company.

This post originally appeared on my blog series on my company website “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup.”

As Mark Cuban says – the market size is almost immaterial

As Mark Cuban says – the market size is almost immaterial

This post originally appeared on the blog series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup” on the Agile Stack website.

The next in our series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup” where we discuss ignoring market share and simply focus on selling and your customers.

Do you watch Shark Tank? If you are in sales at a startup, there is probably no other television show that is as relevant to your life as Shark Tank.

Shark Tank is the television equivalent of a VC conference. Entrepreneurs pitch their ideas to five extremely wealthy people and try to get them to invest. In a startup, if you are not personally responsible for talking to investors, your manager probably is doing it.

My company, Agile Stacks, where I am the Chief Revenue Officer, will never go on Shark Tank. Not because we don’t want the attention of these well-connected investors, but because we are already too well-funded and too large to consider them taking a substantial portion of our company which they prefer to control.

There is one consistent sign that the entrepreneur is going to be rejected by the Shark Tank panelists. It is when the founder starts to talk about how massive the market is for their product. Mark Cuban is usually the first to pounce on this aggressively, and often it is his reason for not funding the startup.

If you are brand new and haven’t sold a single product, then regardless of your targeted market, your market share is 0.00000000% (take that out to an infinite number of decimal places). As soon as you start to sell, the number of decimal places gets fewer, but through most of the time as a startup, you still have well under 1% of your market. You can have an incredibly successful startup and have a meager market share.

Almost every day, the companies Uber and Lyft are in the business pages. They are the big guys in the peer-to-peer ridesharing market. But they are incredibly small in the drive-to-some-destination market (which is dominated by people that get behind the wheel and drive to a destination). On most American streets and highways, not 1 vehicle in 100 on the road is a rideshare car (obviously this varies by city).

Until Uber convinced their first customer to get into a car with a stranger, the peer-to-peer ridesharing market was tiny. It didn’t matter though. What mattered was that the founders thought they could build a company by making it easy, convenient, and affordable to get paid for driving people around in something other than a taxi. They built a product that they thought people wanted, and then they went out and convinced people to try it.

Market share simply doesn’t matter. What matters is getting those first customer purchases and making that customer happy with your service and product. Then get the next purchase (and the next, and the next….). It is only customer purchases that matter and the satisfaction of your customers with your product. 2020 for Agile Stacks is all about traction, I’ve come aboard and inherited a sales team. We rarely discuss market size on my weekly pipeline calls. My drive is to focus the team on working the deal to close. That is what’s important to my leadership and my Board.

Nothing else matters. Just go sell something.

Header photo is courtesy ABC.
Finding the right channel to the market

Finding the right channel to the market

This post originally appeared on the blog series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup” on the Agile Stack website.

The next in our series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup”, where we discuss the ways to check yourself when designing your sales channels.

This post is primarily for my peers as sales leaders in startups in the software market. If you are like me, you probably have years of experience selling for great companies where you refined your sales skills. You were a front line and second line manager for several years. You may have also helped some startup companies that didn’t really ever start.

Now you are in a new young company, and you are trying to sell a product that has never been sold before. There are a lot of very talented people in the startup. Like the fable of Damocles’, there is always an unseen yet prevalent pressure. And what you do to hit your sales forecast is to fall back to old habits. For example, you probably designed your sales force around a similar structure from a prior company. If your background is big software sales like mine then, you brought on a couple of big hitters and enticed them with stock options (because you couldn’t promise them a pipeline). If you are used to channel sales, you may have recruited some sales partners to bring your product to the market.

Whatever you decide, you need to question it. Here are some ideas:

Direct Sales

  • What are all the pre-sales activities in my deal cycle? If you are in the enterprise software market like my startup, Agile Stacks, and have a platform on new technology like containers, Kubernetes and Infrastructure-as-Code, then consider part of your deal cycle will require education almost as long as closing the sale. Consider the time burden you need to carry to educate. Also, consider how market forces such as analysts or journalists can shortcut these pre-sales activities.
  • Can marketing create 3x in demand gen? This one is really all about the math. Having a good (not great) marketing team to find your customers are is critically important. Make sure that you are teaming with the CMO to ensure messaging is in sync, and a frictionless strategy is in place for campaigns. Every marketing person I have ever met dislikes being considered part of sales, however, they love being part of the revenue equation. Going with a direct sales model demands that marketing be part of the whole process regardless of departmental assignment.

Channel Sales

  • Am I selling lipstick or am I selling machine learning automation? Obviously, these are completely opposite product categories. Whether you are a consumer product or enterprise offering, partners and alliances can be useful if you feel that sales velocity can be better achieved by the reach of players already established in the market. Also, do a quick read of How to find the perfect partner as a SaaS startup from my Business Development peer here at Agile Stacks.
  • Does my product require a heavy service implementation to it? My very strong opinion is that tech startups should never compete in the systems integrator market (unless your startup is a system integrator). If investors see an imbalance in your revenue model (e.g. services is greater than licenses) then you are a less attractive investment. The solution is to let partners handle the implementation.

OEM Sales

  • Are they big enough to make an impact? Since we at Agile Stacks are in the new category for DevOps automation, there is still an uphill climb to be well recognized. Luckily, we have a great partnership with HPE because they are an investor. But not everyone get this off the bat. Make sure to do your due diligence in the OEM’s market size and growth trajectory.
  • How far out is the inflection for ROI? Incumbent tech companies will be very interested in what you are doing but don’t be fooled – the negotiation is a very long road. Ask yourself whether the time and effort is going to help sales this quarter or next year. Startups cannot afford to graze. Find OEMs that fill a gap. For example, I look for conversations with our brethren in the hardware space because they are great at making stuff that goes in racks. And I make great stuff that runs Kubernetes in those appliances.

Nothing guarantees a failed startup (or a startup that didn’t start) like no revenue. There are a lot of reasons for a startup to not start:

  • Developers are not as good as they thought, and the product just simply doesn’t work.
  • Marketing missed the market and didn’t know what prospects would spend money on.
  • The CEO and CFO couldn’t convince investors to give the company time to mature.

The worst one though is your fault as the VP of Sales or Chief Revenue Officer – you didn’t set up the right way to sell the product.

The good news for the company is that you can be fired and your replacement might have the trust of the investors to have enough time to fix your mistakes.

Or, maybe you should be flexible. Don’t set up the sales channel that you are familiar with, but instead develop the right sales channel to make your product fly off the proverbial shelves.

Let me close with a reference to Episode 24 of Reid Hoffman’s project called Masters of Scale. In this episode, he interviews Mark Pincus, Founder of Zynga. The resonant quote from the interview, “I believe you have to be relentless about pursuing a big opportunity — and ruthless about killing your own bad ideas along the way.” Flexibility and experimentation is key to success when you are selling a product that has never been sold. Don’t be stuck in your ways. Design a sales model that works for your product even if it is a different model than what you’ve done in prior companies.

Header photo “Indirection” by virusslayer 
The pitch you want to give, yet need to create

The pitch you want to give, yet need to create

This post originally appeared on my company blog series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup”. In this post, let’s talk about the challenge of doing a sales pitch for a product that has never been pitched.

Every day at a startup has challenges. You know this. That’s why being a founder or a member of the founding team can be very exciting. Having been in your shoes, I find that developing the sales pitch can be both heartbreaking and exciting. Starting from scratch and being ready to take on the world is noble, yet the downside is having absolutely no historical examples to jumpstart the creative process.

You may be lucky. Your software startup may be biting at the heels of one or more big competitors. If this is the case, you simply position yourself against their value proposition and say that you are better at something then the big guys.

Maybe you are also cheaper than the big guys (I hope not because pricing can always be lowered due to competitive pressures). Creating a value proposition that is “cheaper” may not be enough to differentiate you in the long run, but there is no question that it can be an advantage if your cost model still allows you to be profitable.

Do Not Internalize Doubt

But what if you need to create a unique value proposition and you cannot copy the value proposition of anyone else? What if your offering is so unique that it is hard to find another company and copy their idea?

First of all, if you are so unique that no one else is doing this, are you too unique? Is there anyone to actually sell to? Did you identify a missed goal that no one else can see, or is it a market that isn’t really there? Do you have a solution looking for a market, or are you in a market looking for a solution? This is really important, and I discuss it in my book, Eliminate Your Competition since competitors prove your need to be in the market. If you have no competitors, you may not have anyone to sell.

By the way, these questions come from many of my successes as well as failures. In my career, I have been fortunate to have amazing mentors. If you have them too, see if they can do a thirty-minute coffee break with you. Ask them your questions. They may not have the immediate answers you seek, but they will have encouraging words that may lead to somewhere you had not yet considered.

Another consideration is to find peer founders at your incubator or accelerator. An obvious cautionary tale, please rephrase your questions so as not to give away any intellectual property or competitive advantage. Polling your peers does have the advantage of boots-on-the-ground knowledge. Having founders who are in the thick of operations and execution will get you another perspective.

Do Something About It

Before your first customer order, you need to use the time-honored practice of A/B marketing. Whereas, my prior suggestion focused on opinion gathering, now I want you to put some of that knowledge into actual use. You should have enough material by this point to create a compelling story.

The downside of A/B sales pitches is that you run the risk of completely blowing a sales pitch to a prospect you desire. That is fine as it is almost as important to understand what NOT to say as it is to understand what you should say. After all, we all grok that “No” is never final and you can always go back to that rejection and explain that you didn’t explain it well and ask to speak again.

Once you have closed a few deals, then you need to have positive feedback from those early adopter customers. To ensure you are truly addressing a need that no other company is solving, you need customers to part with their precious cash in return for your product. Nothing else will prove your value proposition as well as cash.

After you have those first 5-10 customers, ask them what your value proposition should be for your company and product. They are probably not marketing folks with exceptional abilities to write concise and pointed value statements, but they can give you the essential words or philosophies. Hire a copywriter to take those basic statements to craft a message that is unique to you and epitomizes your message.

This method was recently discussed in an article on First Round. The article is about the email marketing success of Watsi. Grace Garey of Watsi explains: “For the longest time, we had it in our heads that people donate on Watsi because they are moved by a patient photo or story and they act on impulse. When we started to see droves of people sign up to donate continuously through the Universal Fund, we realized that users’ motivations were really varied and there might be new ways to reach them we hadn’t ever thought about. We didn’t expect that people really bought into a much broader vision for what Watsi was about — that they didn’t want to just help the person whose profile they were looking at, but underserved patients in general.”

Watsi found a value proposition for their fundraisers by listening to their donors (customers). They were able to learn from those successes to fine-tune their value proposition. You can do the exact same thing with your startup.

By the way, you should seriously check out Watsi. 100% of your donation funds life-changing surgery. It is a great organization, and you can donate here: https://watsi.org/crowdfunding. I don’t have any relationship with the charity, but I am seriously interested in making the world a better place.

Header image Photo by geralt (Pixabay)
I Need Leads!

I Need Leads!

This post originally appeared on my company blog series Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup on the Agile Stacks, Inc.website. The next in my series, I get down to the brass tacks of how every morning likely starts out for you. Hang in there because even veterans start here.

“I need leads!!!” Did any salesperson not say those words?

It is even more frequent with a startup.

There are no leads. There are very few references (maybe none). The product is relatively unproven.

It takes a unique customer to buy from a startup, and it takes a special sales team to work for a company that has 0.00000% market share.

Sure it is exciting to build something from scratch. If it works, it will be incredibly rewarding (hopefully personally and financially). You rolled the dice! You are all in!

But even with all of that excitement, it is still hard work. The leads are not there. There is never enough.

As the VP of Sales, what are you going to do? Not only are you the lead salesperson on all big deals, but you are also the cheerleader and motivator for your sales force.

Every day is straightforward even though it is tough. Here are my thoughts that get me through the day.

You Are Going To Work 80 Hours A Week

OK, if you didn’t already know this going in then let me spell it out – you can kiss your significant others goodbye in the morning and then kiss them goodnight before you go to bed. That’s about as much time as you are going to see them. No, I don’t mean you are in the office fourteen hours a day. In sales, you are on the phone all the time because of the time zone differences. So up early for east coast then calling late for the west coast. And when that really big prospect comes in the door, the hours don’t matter so much as building that relationship at all costs and all times of the days. It’s just the way it is.

You Are Going To Network With Everyone

I really don’t think you get much advice on this. You are going to call *everyone.* That goes from grandma and uncle Joe to the highest level target audience you can get at a prospect. So don’t leave any stone unturned because you simply never know who is networked to whom outside your immediate Level1 LinkedIn connections. For example, our head for BD is an adjunct at his alma mater. Through other professors, we now have a potential market in the education sector that we never imagined could be profitable. And it just so happens that professors are a great hunting ground for enterprise software.

You Are Going To Attend Every Show

Let me qualify this statement…. attend every show you can access free of charge. As a startup ourselves, the glamour of hitting the largest shows in our market is very tempting. So tempting that I probably flood my VP of Marketing’s inbox with so many suggestions that I think he is now blocking me (he is my editor on this blog, so we will see if he leaves that line in the post).

The point of marketing events is not to spend money on sponsorships. The point is to meet people in your market face-to-face so they see you as a key player. In sales, we have to be everywhere at once, or at least give the perception that we are everywhere at once. I recommend getting as many free expo floor passes as you can and network with a purpose.

  • Educate everyone on what you do.
  • Listen to what they are saying about you.
  • Listen to what they are saying about your competitors.
  • Make your pitch better on the follow-up with this person.
  • Find a lead to close!

You Are Going To Cold Call For Hours

Enough said. Look at my last two bullet points. Leads take time and hard work.

You Are Doing Cold Email For Days

Statistics show that somewhere between six to seven touches are required before a prospect makes any real decision about you. We live in an era of omnichannel sales and marketing. Use it to your advantage as low-cost ways to keep your prospect thinking about you. Also, it’s just a polite thing to do to call someone then send them an email afterward even if you got their voicemail.

You Are Going To Do Whatever You Have To Do

This almost goes without saying, it all bubbles up to that one line. No job is below or above the VP Sales. Whatever you have to finish TODAY, you must do. That means sales is building their own pitch decks using canned templates from Prezi or PowerPoint. There is no marketing team that creates aesthetically phenomenal templates for you like in larger companies.

Or in some cases, you are the social media team by retweeting relevant articles to your market that you hope will show prospects you are bigger than you actually are. Just this week, I received kudos from my leadership for being the best employee advocate on social media. Follow me on Twitter at @soshaughnessey and on LinkedIn. It takes minutes out of my day, but the traction I am getting with thought-leaders is priceless. And it doesn’t hurt I am up 400%+ on impressions. Additionally, these touches show prospects that I am passionate about my value proposition as they connect to the value points I tweet about. I know this is an indirect form of lead generation, but it is lead generation nonetheless.

You are also going to spend writing or critiquing marketing materials (I am finishing this post on the Monday of a 3-day holiday weekend). You are going to be involved in the web site redesign project. You will be involved in marketing events. All of this leads to getting the messaging right so when you make contact then you get the leads because you are prepared.

There is literally nothing that you are not going to do as the VP of Sales and that is exactly why you want the job. In a young startup, there is no job that is this invigorating or this demanding. You know the work is long, but you also know the rewards can be achieved.

Even if yesterday sucked, it doesn’t matter. Go out there and do it some more. You are in sales. Go make it happen. Tom Hank’s character in a League of Their Own said it best, “There is no crying in [sales].” And from another Tom Hanks movie (Apollo 13) “Failure [in sales] is not an option.”

Header Image by Pexels from Pixabay

Don’t stop learning when you are in a software startup

Don’t stop learning when you are in a software startup

This is the first post in a new series of thoughts on selling software as a startup titled “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup”. It first appeared on the Agile Stacks website where I am the Chief Revenue Officer.

My postings on this topic won’t be on a guaranteed schedule but will be the random thoughts as the Chief Revenue Officer for a young company selling enterprise infrastructure software. This first post will be to give a little bit of background on myself, but more importantly, to offer some advice to salespeople that are just beginning their career in business-to-business or enterprise sales.

The software sales industry has evolved dramatically since I first started selling software. In the mid-80s, software was primarily written to add value to hardware. Most of the computers in those days could heat a room (or a building) and had the processing power that was less than the phone in your pocket. The real commission money came from selling the hardware, and the software was almost always a giveaway as part of the deal. Back then, a cloud was a visible mass of condensed water vapor floating in the atmosphere, typically high above the ground that blocked the sun and sometimes dropped rain to ruin your golf game.

My alma mater is Rose-Hulman Institute of Technology where I graduated with a bachelors of science in mechanical engineering. Most of the time that I was a student I knew that I was going to be a lousy engineer. I love science and physics yet I despise the redundancy of a 9-to-5 office job that many young engineers experience. My tenure as an engineer was over before I walked off the graduation stage with my degree. I had accepted a position as a Sales Engineer with The Allen-Bradley Company of Milwaukee WI.

In all of the jobs over the years, accepting a position with Allen-Bradley (A-B) was probably the best career decision that I ever made. A-B had just been bought by Rockwell and would eventually change its name to Rockwell Automation. At the time though, A-B was investing heavily in college engineers to become salespeople – they wanted smart, raw talent that they could mold. I moved to the company headquarters in Milwaukee, WI and began an 11-month sales training program under the wise mentorship of the A-B sales experts.

Nearly every sales trainer explains that everyone sells. They give examples of selling from the youngest child trying to get a piece of candy to adults convincing a spouse for a new set of golf clubs. This is true, but unfortunately just because everyone sells, very few people do it really well. The sales profession is one of the hardest professions in the world, and enterprise sales is among the hardest of all types of sales positions. Going through an 11-month training program probably cut 5 years off of my on-the-job training.

Few companies today can make the incredible investment that A-B made in me. I wish I could return this favor by doing the same to college graduates, but unfortunately, it is a different world. In that 11 month program, I learned many skills that I still use today. For myself and many others, this was our masters degree in sales. Here are some of the timeless skills that today make a better salesperson:

  • How to plan a sales call so that everyone on my team knew how to succeed
  • How to explain the benefits of a product rather than just its features
  • How to understand a prospect’s business
  • How to build a relationship with a customer to make it a win/win relationship
  • How to manage the entire business with a customer, not just the next deal
  • How to effectively team sell to a customer
  • How to deliver a presentation that it is motivating
  • How to write effective letters
  • How to negotiate and close a deal

Allen-Bradley put me through classes, seminars, and practice sessions for months. I was tested weekly to affirm that the information and techniques stuck. I made joint calls with seasoned salespeople having decades of experience. These were the masters, and I was excited to be along for the ride. Eventually, I made sales calls. The masters watched. Their feedback was foundational to my growth. A lesson I took away – find a great mentor and never let them go.

In addition, Allen-Bradly was patient. This built a strong foundation to be the best salesperson that I could be. Teaching that continuous learning and continuous improvement creates more future opportunity is a value I cherish today. I pass this knowledge to you – my sales peers. You need to master the craft in the profession that you have chosen. Embrace the process of learning and improvement.

It is often cited that you need 10 years of doing something to be an expert. I am sure this is true, but I have seen salespeople that have decades of experience and still are not experts in their craft. I theorize that this is because they are not continually learning and continuously striving to improve.

While I am unable to train a group of young and eager college graduates for a year, I can pass on my experiences and learnings. That is my goal for this blog series. I am hopeful that it will be helpful to salespeople of all ages, new managers trying to learn how to motivate others, and entrepreneurs trying to start the next great software company. I hope that you will subscribe to the feed of this series so that I can help you sell more software and offer benefits to your customers.

While reading this series, I hope you gain some insight into the above bullet points and I hope that you learn a little about what it takes to start an enterprise software company from scratch.

If you like this series, you may also want to read my book on sales, Eliminate Your Competition. You may purchase my book from your favorite book retailer. The ebook version is available at the most popular retailers such as Apple, Amazon, Barnes & Noble. The paperback version is also widely available at such retailers as Amazon, Barnes & Noble, and Books A Million.

You should also subscribe to the series “Skinned knees—what an MBA didn’t teach you for rebel sales in a software startup” on the Agile Stacks website.

Header image by Gerd Altmann from Pixabay