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How do you leverage a career move in Sales from SMB/Mid-Market to Enterprise?


Ian MacVane Brooklyn, NY

What does a recruiter look for when hiring a candidate to an enterprise role?

12 November 2020 5 replies Career Advancement



Leanne Drennan Chicago, IL

Hi Ian, I have a slightly flip answer for you. Selling is selling. You can go with confidence into a sales role in an enterprise because sales is inherently about building trust between people and establishing the business value of your product or solution. Those two things are the same no matter the size of the business you are selling to. What may be different is how the sales organization works - the enterprise will likely have more processes, more sales roles, and more products/offerings. You may also need to call on clients who manage larger companies so make sure your business acumen and financial acumen are solid. Recruiters look for success so take your SMB/Mid-Market success with you and build the story of how you succeeded in SMB/Mid-Market will also make you successful in a larger enterprise world.

12 November 2020 Helpful answer


Karen Lau Bedford, NY

Hi Ian,

I started working in new business, so think knocking on doors, and SMB. I thought that was one of the toughest positions to be in because you have to be innovative, constantly finding angles, knowledgeable about multiple products and business industries, and thick skinned because of the number of rejections! So that energy and thinking you bring to the table is the icing on the cake to what all sellers have, which is the ability to build relationships with clients through listening and doing right by your client. Enterprise accounts to me, involves engaging and collaborating with multiple teams, both within your company and the clients (and maybe even other partners), on the multiple projects and sometimes there is a certain governance you have to abide by. It has it's own challenges, but what you bring from SMB absolutely helps define who you are and how you can continue to grow.

It may be helpful to talk to some enterprise sellers and teams to get an idea of how they operate and focus to help you with your story.

Good luck!


John Cattani Cumming, GA

Hi Ian and I've worked both. While the two are similar, there are nuances that are more common in Enterprise Sales - on average: larger deals, longer sales cycles, more competition, greater barriers to becoming an approved vendor (if not already a vendor), greater propensity to RFPs / RFIs. So when speaking to a recruiter, emphasize ability to create trusted partnership and business outcome based activity fast, and sustaining that long term in a competitive environment. If the sales job is hunter for enterprise, explore how they typically overcome the barrier to contracting / vendor management and what about the product / service is compelling enough to do that. Also prepare some SART responses on overcoming situations in a complex environment. You should have all of your examples in SART format for interviewing purposes.


Jeff Martin Ashburn, VA

I’d suggest that you network at the target company or industry. Use LinkedIn to find people already working there and reach out to them. Ask them the process they used to get hired and ask them to help you navigate the hiring process and if they are willing, ask them to submit you as a referral. These activities require much more time on your part but in my opinion would greatly increase your chances for success. Good luck!


Christopher Bazinet Westbrook, CT


Personally, I think that the objective for SMB/Mid Market or Enterprise is the same - improve the client's ability to serve their customers with a reasonable financial return. SMB clients, as they are smaller, can be easier to navigate. Enterprise clients often have larger IT (and other) organizations.
It's been a long time since I was in the enterprise sales business, but I assume that a key capability for a candidate would be a proven ability to navigate a complex organization and to achieve results across a wide variety of interests.
Perhaps you have experience doing this in the US Army. That's larger than most enterprises in the world.
I'd work on articulating some examples of your success in pulling together multiple competing interests in a large organization and accomplishing a common objective. This is how large companies work.

Good luck in your endeavors and let me know if I can help, Chris

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