Author: Sean O'Shaughnessey

Navigating the move from enterprise executive to 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. Small companies are not a reprieve from corporate life; they live on the razor’s edge of “scale or die.” Time and mediocrity are enemies. Small companies 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?

Find Your ‘Who’

I was introduced to my last 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

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 small company 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 the new normal. You must create more with less, fast and with laser-focus on impact. Small companies 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 appeared on my blog dedicated to helping salespeople generate more commission.

Do you watch Shark Tank? If you are in sales at a young or small company, 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.

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 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.

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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, 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:

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Every day at a small or medium-sized company has challenges. You know this. Having been in your shoes, I find that developing the first 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 company 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?

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

It is even more frequent with a startup or small company.

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 or a small or medium-sized company, and it takes a special sales team to work for a small company.

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.

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

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My postings on this topic won’t be on a guaranteed schedule but will be the random thoughts as the outsourced VP of Sales for small and medium-sized companies. 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 Bachelor 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 my blog about my book. This particular post was based on a post that exists there.

Header image by Gerd Altmann from Pixabay