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To sell for a big company or a small one - Which one is right for me?

· career

The question I've been asked three times in the past two weeks: “I’m really struggling between two potential roles: a sales role with (big-a** company) or with (tiny-little company). How should I be thinking about this?”

At its most basic level, it's like deciding between a cruise ship and a speed boat. Both pretty cool, but for different reasons.

Given that I’ve sold and led in both, here’s my take: My Top 8 Pros of selling in each environment.

What do you think? What am I missing?

My top 8 pros of selling in a bigger company:

1. The pay: These organizations typically can afford to pay more - better salaries, higher upsides, stronger benefits packages, and bigger perks. If they’re already publicly held, stable stock-purchase plans are nice, too.

2. Formal development: The larger the organization, likely the more structured, formalized and resourced the training. This isn’t always the case, but it’s much more likely to be true.

3. Resources: Your job is your accounts. When an RFP comes in, guess what? It’s likely there’s an RFP team to help you answer it...and put it into what looks like a professionally published manuscript. Your deck? There are designers to help put that together. Need tech support for a meeting. You’ve got it. You sherpa the deal, quarterback the resources, and spend a greater percentage of your time on selling activities versus 'building' activities.

4. Name recognition: Prospecting is easier when the prospect has heard of you. It’s an advantage when closing deals, too. If you’re a well-known organization, the buyer’s perceived risk is typically lower, meaning ‘credibility’ and ‘references’ are a couple less things you have to worry about slowing or stalling a deal.

5. The logo on your resume: I can’t tell you how many times an executive or entrepreneur has told me about someone they want to hire, “She comes from a LinkedIn background”. Exchange “LinkedIn” with “Salesforce”, “SAP”, “Oracle”, etc. The “ExactTarget” and “Salesforce” names on my resume were compelling during the last time I was a part of a fundraise with the private equity firms. It’s perception - I’m not saying it’s correct. It's kinda like having Harvard on your resume. Doesn't necessarily mean you're better...

6. Stability: As mentioned above, do you want to be on a cruise ship or a speedboat? The bigger the company, typically the more stable the day-to-day. Startups can be rollercoasters; One day you’re selling a high-impact, highly involved solution. The next? A high-velocity solution. Some people love that...and it’ll drive others nuts. The later the stage, the lower the risk of organizational failure. Big companies can fail. Big companies experience layoffs. Big companies shutter entire groups. But on the whole, your risk is lower in a big company.

7. Easier to hide: I literally had a friend of mine tell me they want to go to a big company, hide in the weeds, make money, and not be noticed for a few years while they spend more time at home with the wife and young kids...then they'll go "all in" again later. It’s an awful lot easier at a big company... especially if you meet expectations and do what you say you’re going to do. I don't recommend that reason, but if it's you, it'll be easier in the bigger organization.

8. Ohhhh, the parties: Have you seen the Dreamforce speakers and entertainers for this week? They’re getting paid for one performance more than you are for the year. Some of the most impressive concerts and parties I’ve ever seen have been during my days at SAP. Ridiculous parties. I’ve seen Metallica, The Foo Fighters, Train, Ray Charles, John Mellencamp and a few other awesome bands while at larger sales organizations.

My top 8 pro’s of selling in a smaller organization:

1. Impact: Everything you do has an impact. Your opportunity to build, participate in strategy, have a seat at the table, and see the fruits of your labor impact your customers and your co-workers are dramatically higher in a smaller organization. Simply put, this alone is why I love them. I always felt that if I did really well in a big organization, nobody really noticed. I might show up in a list somewhere. My manager might recognize my efforts at a meeting. But your success (or failure) doesn't show up visibly in the company's overall performance. If I sucked, that didn't show up, either (i.e., easier to hide in a bigger organization). I enjoy having my efforts directly impacting the organization's performance.

Side note: At a big company, you may get to go to "TPC" (Top Performer's Club - a "vacation" with your peers). You probably won't have that opportunity at a small organization. For me, I couldn't stand TPC. I want to be with my wife and kids. If I have to leave my kids for a vacation, I prefer it just be with my wife. I dislike forcing my wife to hang out with piles of other salespeople I barely knew while away from our kids. I know...that's maybe just me.

2. Visibility: You’ll see all the elements of an organization working together. You’ll see and learn how the product team operates, engineering, client success, marketing, senior leadership, and watch their decisions and the impact on your individual effectiveness. In a larger organization, those decisions are so buried in your training, you don’t see them. In a smaller organization, your voice matters. At PowerReviews (initially small), our new SDRs were taught to talk to prospects and sell appointments, all while seeing the rest of the organization. While many next moved into Account Executive roles, others moved into marketing, product, business development and client success.

3. Recognition: If you’re good at what you do, you will be recognized across the organization. Everyone in the organization will know who the top rep is. At a big company, the majority of the organization will have no idea. There is no feeling of "I'm a small fish in a giant pond" in a small organization.

4. Opportunity: In addition to recognition, being seen means more opportunity for career growth. In some smaller organizations, the top performers were expanding responsibility or taking on new challenges within the organization much more frequently. The smaller the organization, the more cross-organizational recognition, and oftentimes the faster it takes to achieve promotion (assuming the company is growing and evolving). This may also mean you walk out of your tenure with a smaller organization carrying a more impressive title than if you went to a large org. However, some large organizations pass out VP titles like a you never know.

5. Celebration: A $1M revenue org grows $1M, it doubled. A $1B revenue organization grows $1M, it sneezes. Startups and early-stage organizations feel like families. You know everyone, and they know you. And when there’s a success, you all celebrate. We celebrated every win. At PowerReviews, the deal celebrations were epic when we were getting started. We had a company-wide champaign toast when we closed our biggest deal. Everyone in the company in all functions knew when a deal closed. When big deals close in big companies, there may be a Slack message somewhere...and the small ones go unnoticed.

6. Upside: The higher the risk, typically the higher the reward. While you may be giving up some salary and OTE, if the organization you’re in experiences any sort of successful exit, whether it be an IPO, buyout or acquisition, if you’ve played a key role and been with the organization from the beginning, you’re gonna like the payout. (Just be sure to get equity when joining...I believe every employee in an early stage organization should be granted some equity in the organization.)

7. Ownership: In a selling role, you own your territory. There are no overlays. You'll know when someone in your organization touches an account of yours. You own it. You are involved in the communication to it. You own the strategy around maximizing it’s potential. In a larger organization, you probably don’t. In some large organizations, there may be 5-10 people calling on your your own company!

8. Control: In each large organization I worked in, I wasn't a big fan of the politics, the bureaucracy, the hoops/red-tape, the scrutiny, and the cover-your-a** requirements. The path to getting something done in a smaller organization is always straighter line.

As you can see, it's personal preference. There really is no correct's all you. Prioritize where you are in your career, what you can be truly passionate about, and which of these elements is most-to-least important to you. I love the build. I love making an impact. I so appreciate the foundation large companies built in my career. I learned so much from them, and applied them to the small organizations I've led.

What have I missed? Comment below...would love your take.

Did you see the news? The Transparency Sale was recognized as the 2019 Best "Business: Sales" book at the 17th Annual Best Book Awards.

It's sales kickoff planning season. I'm booking up quickly - but would love to participate in yours. Check out my speaking & workshop pages for more info.

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