As any sales leader will tell you, enterprise sales are high risk, high reward — but preparing representatives to approach such large-scale, lucrative prospects often requires both a steady hand and a gentle touch.
Whereas selling to mid-sized or small companies typically falls within the comfort zone of any successful sales rep, preparing to handle enterprise sales can be a daunting proposition for even the most experienced reps. As a result, most B2B startups start small, favoring short sales cycles and pitching businesses where one founder or a handful of stakeholders are the sole decision-makers.
Fortune 500 customers, on the other hand, are often exponentially more complex on a logistical level. Enterprise sales reps aiming to close game-changing sales in the six- or seven-figure range — the kind that can make or break the future of a small startup — should expect longer sales cycles and repeated pitches to multiple high-level executives. But most importantly, they should expect the unexpected.
Below, two sales leaders at fast-growing tech companies discuss their approach to coaching salespeople toward enterprise sales — an important goal in any rep’s individual career growth that can also signal a promising future ahead for your organization as a whole.
Lusha enables B2B salespeople to identify, engage with and close deals using its crowdsourced data community and sales intelligence platform.
What are the biggest differences that a growth or SMB sales representative will experience when selling to enterprise organizations for the first time?
The biggest difference is in the process. With SMB, your champion is also the decision-maker in many cases. As you sell upmarket, your champion remains important, but multithreading your approach is even more critical. Selling to enterprise requires the salesperson to dig deeper, ask more questions and truly understand the buying process. Building advocacy, rapport and buy-in across the organization is paramount. Tools that may have worked to provide urgency or speed up a deal within SMB have less of an effect on enterprise. A deeper discount or better billing terms won’t speed up a security review.
In addition to the difference in buying process, the pace of the sale is another change when moving from SMB to enterprise. Larger organizations have more hoops to jump through. A salesperson transitioning from SMB to enterprise will need to reset their own internal expectations based on the new motion’s sales cycle. Instead of a one-call-close mindset, the purpose of each call becomes to inch the deal closer to the finish line.
How can sales managers prepare sales reps to handle those differences?
Sales managers can best prepare reps for enterprise by making sure that they nail the discovery phase. The common element of all sales methodologies — at least the good ones — is that the discovery phase not only uncovers pain that can be solved by the solution being presented but, more importantly, uncovers what has the potential to kill the deal. It can feel unnatural to ask a customer about the last time their company bought software or about the inner workings of the procurement process. The role of a sales manager is to ensure that their reps are comfortable asking the uncomfortable questions, so as to leave no stone unturned.
The short answer is that you never know until you play the game.”
How do you know when a sales rep is ready to start selling to enterprise clients?
The short answer is that you never know until you play the game. A strong enterprise rep must showcase the obvious key characteristics, such as intellectual curiosity, a growth mindset and the desire to win. Before the game, however, practice is key. Ride-alongs with senior reps and roleplays with management can build a valuable foundation. Because enterprise is more strategic in nature, being able to articulate an account plan is another way to gauge a rep’s readiness. Can the rep map out the deal from first call to close? What roadblocks can they foresee? How will they overcome objections? The best enterprise reps have the ability to play out multiple scenarios and have a plan for each. As a leader, it’s important not to overanalyze things. Provided your total addressable market is large enough to allow for a few hiccups, don't be afraid to let your rep out into the wild. The best learning comes through experience.
Gradient AI’s software-as-a-service platform brings state-of-the-art artificial intelligence and machine learning solutions to the insurance industry,
What are the biggest differences that a growth or SMB sales representative will experience when selling to enterprise organizations for the first time?
The complexity of an enterprise sale will be the clear difference. The seller will have multiple client stakeholders, decision-makers and influencers that will all need to be aligned to move an enterprise deal forward to closure. This often extends the sales cycle beyond what a seller might experience in the SMB market. Typically, enterprise sales have higher visibility and higher dollar amounts. Based on this, an economic model or business case or ROI investment justification is a necessity to move any enterprise deal to closure.
How can sales managers prepare sales reps to handle those differences?
Consistent coaching throughout the sales process will enable the seller to overcome the challenges and objections associated with an enterprise sale. It’s important for sellers to always have an end in mind and deliver value during every client conversation. Specifically, for every client interaction, define the desired outcome and ensure it maps to the overarching deal progression strategy and plan. Have a plan to get to the desired outcome for each interaction. The sales manager should be consistently coaching the seller on how to execute on the deal strategy and make every client interaction valuable.
Have a plan to get to the desired outcome for each interaction.”
How do you know when a sales rep is ready to start selling to enterprise clients?
As sellers progress in their sales journey, experienced sales managers clearly see and recognize this. It’s important for sales managers to have a plan to coach each seller based on their skill level and experience. Overachieving sellers will become more independent, and their sales manager’s coaching and support should respect this progression and pivot to support the seller in ways that will ensure continued success.
