March 9, 2023
The career trajectory of a seller
Enterprise sales is one of the most lucrative individual contributor positions in the tech world. Those who navigate a career as an enterprise seller can make enough in a decade or two to become financially independent and have complete choice in what they do next.
But beware – if you make bad career decisions and just hop from gig to gig chasing the next shiny object, you will not only be short-changing your personal and professional development, you might be leaving hundreds of thousands or millions of dollars in earnings on the table.
There are five levels in the career path of an individual contributor seller. Each builds its own skills, offers and opportunities and comes with significant trade offs.
Here is a rundown of each level. The list does not include SDRs/BDRs as they are typically not full cycle sellers.
- Mid market
- Strategic Accounts
- Key Account Director
SMB is the typical jumping off point from SDRs who graduate into their first full-cycle selling role. The accounts are small, it is much easier to get to decision makers (often the CEO), the cycles are short and there are tons of them. The trade off is that the deal size is very low.
The selling motion is simple, formulaic, transactional. SMB and Mid market are the mainstays of the velocity sale. This is definitely the zone where sales is a numbers game, but hey, you gotta start somewhere and newbie reps can cut their teeth here without doing much damage.
The mid market segment offers reps their first level of added complexity. The organizations are still quite flat – it’s a short jump between managers and worker bees so while corralling the small number of stakeholders needed to drive a decision takes more work than with SMB’s, it’s much more manageable than in the senior segments.
Deal cycle length and deal sizes start to grow. Reps learn to bring in other team members to help them sell – presales, maybe their direct manager.
There are many definitions of the enterprise segment. For our purposes let’s say it is $1B in top line revenue and up. At the enterprise level, things get much more interesting. This is the biggest jump in terms of learning how to manage multiple customer stakeholders across ranks in more hierarchical organizations. It’s also the biggest jump in OTE compensation (over $60k) if you compare the Repvue graphics for mid market vs. Enterprise OTE.
But here are the tradeoffs
- Sales cycles are long – 9-18 months.
- Decision-makers are harder to access.
- Deals are harder to forecast.
- Reps spend much more time managing internal stakeholders, updating internal executives on status, next steps, etc.
Here’s maybe the biggest burden – because enterprise sellers are the most expensive position in the sales org, they have increased scrutiny by management as it takes at least $300,000 ARR to support one rep.
Underperformance can quickly lead to being put on the dreaded PIP and soon you’re out the door.
Key skills to learn:
- Creative Outreach – differentiate beyond cold email and phone
- Multi threading – continuously creating relationship redundancy
- Deal team management – big deals have big deal teams
- Executive engagement – enterprise deals don’t happen without executive engagement.
Once a rep has learned foundational enterprise skills and has a few significant deals under their belt they can move on to Strategic Account manager positions. Strat AEs have fewer accounts, typically 3-5, with revenues of $10B and up.
Winning at the Strategic Account rep game is all about masterful account management. Most accounts will be existing customers and your job is to capture TAM and deepen the relationship. That means your job will be to enter the world of Executive Whispering which goes beyond just the executive engagement mentioned in the mid market section to the level of creating champions that will sell and gain customer stakeholder buy-in when you are not in the room.
is the art of working with executives on both sides of the table and something I teach in my masterclass.
In my experience, Strat reps and KADs are the most fun, the highest stakes and by far the most profitable roles in B2B sales. You live and die by fewer opportunities but those deals are much larger and you are dealing with much more senior stakeholders.
The selling process is much more strategic than less senior selling roles. So much of the strat rep’s time is devoted to learning their accounts business models and interfacing with executives to better understand their mandates, motivations and personalities.
Another big skill learning at this level is how to build a customer-specific value story. This goes well beyond storytelling of how your solution solved big problems for other customers.
Great value stories come from quantifying the specific value a customer would get from your solution based on process improvements.
Modern sales motions more often than not expect the strat rep or KAD to lead solutions teams and/or value engineers in efforts to diagnose problems their customers face and to build a professional-grade business case that will stand the test of any CFO.
Key Account Directors
Key Account Directors (KADs) are top of the food chain in the world of B2B sales. It is a destination role which, once reached, many reps never leave.
Especially at public tech companies, most KAD roles are for a senior individual contributor seller to manage the overall relationship with a single, global account.
Although it is true that the KAD is an individual contributor, the role is like the CEO of the account relationship.
When I was a KAD at Oracle no one reported to me but over forty people “worked for me” across sales, presales, marketing, Customer Success, etc.
The KAD’s job is to align with their customer’s executives around the customer’s strategic vision and imperatives for a three year period and then to get all the product or regional reps to march in line with that vision.
If you ever reach this level, you will experience much more exposure to your own executives, which can be a two-edged sword.
Your own senior executives can make or break big deals with their focus and engagement. They can also be relentless taskmasters, demanding constant updates and documentation from you, which can be exhausting over time.
I have experienced both. At the end of the day it is better to have your senior execs in the boat selling with you than not. Even if they sometimes make you burn the candle at both ends.
And if finding and closing mega deals is on your professional bucket list, it is worthy of note that all of my mega deals closed while I was either a strat rep or a KAD.
The trajectory of a B2B seller can take many twists and turns and without visibility into the path, one can get side tracked or stuck. I hope this description of the levels of B2B sellers gives you insight into where you can take your career.
When you are ready there are three ways I can help you get to the next level in your selling career.
1. Mega Deal Secrets – I’ll give you a free copy of the book that started the mega deal movement.
2. The Enterprise Seller community – surround yourself with the most ambitious enterprise sellers in the game.
3. The Mega Deal Secrets masterclass – skip the line and get the cheat codes to closing mega deals by investing in my masterclass where I teach all my secrets to close massive deals.
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