Sales Leadership Roadmap
Congratulations on your new sales leadership role at an early stage company. If you come from a large company, immediately throw out what made you successful there. Don't try to implement their methodology, at least not for several years. Big company methodology will not work in a start-up or early-stage company. It will likely fail within 3-6 months and will cost you your new job a few months after that. You need to let go of what you know or learned and listen to what the market wants. You have two ears, two eyes and one mouth, use them in proportion to listen and observe more then you speak. When you do speak, only do so to ask questions and learn more. Do not try to tell customers what they need instead sell them what they want, which will allow you to be more successful sooner. This is the first rule of Product Market Fit (PMF).
Product Market Fit
Many times I have worked for or consulted to a start-up where the VP of Sales used Salesforce, or an equivalent CRM, layered with too many opportunity stages and relied on it for accurate forecasting. The VP of Sales, with pressure from the CEO and Board, ends up pushing their sales team to find deals, using their "Rolodex" (circa 1990's selling style) that are not a good Product Market Fit. You end up with a tremendous amount of documented activity, not selling opportunity. This activity report is generated with little to no qualified prospects to create the illusion of potential business revenue and satisfy the upper powers. Don't fall into this trap. Man (or woman) up and let the chain of command know what the market wants versus what you have to offer (the answer is always in the market). This is the main reason many early-stage companies go through multiple sales teams (and VP's) before they figure out PMF. Often the company is 'fire sold' or goes out of business.
Hiring
Keep an open mind when hiring and jump to hiring your prior teams. Hiring people from large or medium-sized companies like Cisco, HP, Oracle, or SAP, who do million-dollar deals, mostly selling into their installed base, probably aren't going to be a fit for your new home. In the startup world, one million dollar deals, or even one hundred thousand dollar deals, are few and far between. The time spent chasing these deals is futile and rarely results in success. Usually, this occurs because they were not perfect fits (needed an extra feature or two not on the roadmap) or the company was too small to be able to win the deal (i.e. risk adversity by the end-user). Initially, you need many smaller sized "friendly" customers to help flesh out and buy the product, then become a reference. At this stage, you need to build a sales model of repeatability. Hire talented, scrappy, market-makers, not individuals who have spent many years at big companies.
Simplicity
Keep everything as simple as possible. Coming from a big company it's easy to make things more complex than they need to be. In the startup environment, this creates more excuses for failure (denial of PMF). The pricing, pitch, presentation and messaging should be simple to understand. As Einstein once said, "If you can't explain it simply, you don't understand it well enough". Understand what your solution's strengths are and sell to them without disparaging a competitor's product!
Passion
Be incredibly passionate about the problem you are solving and the solution provided. Taking a VP of Sales job for the paycheck just isn't going to work out in a startup. You need to take ownership as if it is your baby too. Late nights and weekends are routine for the VP of Sales in a startup. You will always be on the grid, and your vacations will become "work-cations". You have to BELIEVE to SUCCEED. That authenticity is key to selling the product.
The Management Teams
Pick a company, founder(s), and CEO’s that you are compatible with. Look for someone that will support you in good times and bad. The road crossing the chasm to success will be fraught with challenging times and events beyond your control. There will be spectacular highs followed by excruciating lows. Knowing your CEO and the rest of the management team has your back makes all the difference. Early on, it's imperative for you to interact and collaborate with engineers, product managers and marketing professionals. You should not be isolated from them as you may have been working for a big company in the past. The sales team is important, but the engineers are equally important - especially in the early days of the product coming to the market. If you're perceived as a stereotypical big company sales VP, they will not respect you nor listen to your input about what you have discovered the market needs. They will dismiss you and not add the necessary features or do the product changes the company needs to be successful. Telling a founder or engineers that their 'baby is ugly' takes some finesse and respect. Learn that engineering, product development, and marketing teams are your partners, not your enemies. Inbound marketing is key to the success of an early-stage company. The more you work as a team to refine the customer profile and target market, the smoother the road to success. An inbound lead is much better then trying to cold call your "Rolodex" (I highly dislike this misused, dated term, if you haven't figured that out by now) hoping for a fit. Having a great relationship with these teams is vital to you and the company's success.
Success is Rare
Understand that 8 out of every 10 startups will fail. They fail for many reasons, all beyond your control. Typically, unsuccessful start-ups will have an unfavorable liquidity event (sale), to make the investors whole. Enter employment at a start-up with your eyes open. Increase your odds of success by joining a team that has succeeded a few times, but also learned from its failures.
Pay Up
Do not be stingy or try to use a compensation plan that worked in your big company experience. You need to pay your salespeople above the market rate - pay them to take this risk with you. Your initial compensation plan may need to be based on Management by Objectives (MBO's) rather than revenue. The only way good people are going to come to your company is if you pay them a high commission rate. Early times at a company are the hardest times to make sales, so you need a highly incentivized, mercenary-type sales team.
Teamwork
Your team's success is your success - NEVER forget that. Your job is to create a structure and culture that not only breeds success but also creates a fun work environment. Yes, fun! People produce more and better if they are in a fun, interactive atmosphere. This serves to make employees more productive and loyal. Never be political and don't take credit away from the team to shine the light on yourself, or you will lose the respect of your team very quickly. Nobody likes that kind of manager! Set your team up to be successful and pay them well when they are. Coach them to understand what it takes to succeed in your sales organization. They need to feel like you are there to support them, not to produce fresh CRM spreadsheets to sell up to your management. Being hands-on, not micro-managing, is imperative as a startup VP of Sales. Practicing what you preach is the easiest way to win over your team.
Following the suggestions above will set you on a good path to be successful at a startup, and learn a few new things along the way - which keeps the opportunity interesting and challenging for you. Most importantly, enjoy the ride!