With Big Deals Comes Big Responsibility

For a sales representative, transitioning into enterprise-level opportunities can be exciting. This jump is often seen as a big step up the ladder of professional development, but with bigger deals comes bigger responsibility — and that can be a daunting prospect.

While the basic concept of enterprise sales is the same as that for SMB opportunities, Andrew Knobloch, the SVP of revenue at real estate data company CompStak, believes there is a lot for representatives to learn when leveling up. “While the goal with both targets is to effectively prospect, qualify and close business with organizations, the biggest difference between SMB and enterprise opportunities is in the timeline, strategy and execution throughout the sales process,” he said. 

So how can sales representatives successfully move from SMB sales into enterprise and how can companies support them in this process?

Isabel Reich, the chief growth officer at Lightyear Health, says that strong and insightful leadership is essential to a smooth transition. “Selling at the enterprise level can be intimidating for sales reps and the rest of the team,” she said. “Handling the differences between SMB and enterprise sales all comes down to proactive coaching.”

Upskilling a sales team to the enterprise level is beneficial for both representatives and companies, but this growth doesn’t come without its challenges. Built In New York caught up with five industry leaders to discuss the biggest differences between SMB and enterprise sales, how representatives can prepare for this transition and how leaders can support them on this journey.

 

 

What are the biggest differences that a growth or SMB sales representative will experience when selling to enterprise organizations for the first time?

Most of my sales career has been spent in high-volume transactional sales. Our new B2B team at Wix is my first true enterprise experience, and I’ve realized it takes effort to unlearn ingrained transactional muscles. It is a wildly different task.

Right now, it’s important to fight the tendency to approach our market with an established offering. It’s less about pushing a specific product or service, and more about handing our prospects the microphone and listening to them. This is solution-based selling, so having a thorough understanding of needs is crucial.

Another difference lies in the sales cycle itself. Not only does enterprise generally infer a longer sales cycle, but it also requires us to collaborate with other teams — product, UX, marketing and more — to craft a solution. We’re the advocate for our prospects, so being able to communicate clearly, remain consultative and build strong relationships is how you’ll succeed.

We’re the advocate for our prospects, so being able to communicate clearly, remain consultative and build strong relationships is how you’ll succeed.”

 

How can sales managers prepare sales reps to handle those differences?

We recently had a consultant host training sessions about the art of the consultative sale. This helped our sales team calibrate on the consultative approach and how this would inform our outreach and pipeline management.

There’s definitely a learning curve, so shadowing calls, listening to recordings and watching our own game tapes are crucial. We’re always learning what works and what we can do better. We also help our reps learn how to identify trends and ensure they’re comfortable voicing this to our leadership team. 

Prospect and user feedback is critical as it helps us define our offering. Just last week, we shared a new offering update based on frontline feedback. It’s empowering to know we influence what the offering includes as this enables our reps to have more successful conversations.

 

How do you know when a sales rep is ready to start selling to enterprise clients?

First, sales reps must have a command on what Wix currently offers. When you speak to prospects, you should be able to direct them to features within the current Wix ecosystem to help them better use the tools already available.

You’re ready for enterprise sales when you’re less focused on what you’re pitching to the prospect and more focused on understanding and working with their needs. You must be able to dig deep and ask thoughtful, relevant questions. This information is what guides the other teams when determining how to execute. 

In the end, the procurement process is genuine. Rather than forcing a square peg into a round hole, you’re focusing on solving real problems with custom solutions, which is very impactful.

 

 

 

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 a rep will find is that the enterprise sales process is more complex. There are several extra steps on the client-side — sales reps should undertake more measures, use checks and balances to build credibility, and exemplify the standards that clients are looking for in a vendor. Overall, reps will find that clients dig into more parts of their offerings. 

In SMB sales, reps are able to focus on the product, but at the enterprise level, it comes down to verifying the vendor’s credibility across all components of the offering. It is important to anticipate the questions enterprise-level clients will ask themselves.

 

 

When selling to enterprise organizations, you’re going to get much more scrutiny over parts of the offering because the offering is more than just the tech. You’re now having to sell everything to the enterprise. Reps will find that stakeholders will make or break the deal at the enterprise level, as more opinions and approvals are weighed in the decision-making process.

 

How can sales managers prepare sales reps to handle those differences?

There needs to be a qualitative focus on what you’re doing along each step of the process, so that reps are aware of the potential challenges and are equipped to win each step consistently with support from different teams and strategic training. Reps need to break down each part of the process so that they know how to win.

It’s crucial to be a healthy skeptic in the deals and even more wary of “happy ears” when speaking to clients — hearing something from a customer and, without meaning to, interpreting it into alignment with what you were thinking. Being explicit around the process, identifying potential obstacles and qualifying next steps are all part of the rigor that is table-stakes at the enterprise level.

Empowering reps to coach stakeholders to sell on their behalf internally is much more impactful than simply doing the selling themselves, which is more common in some SMB sales processes. Internal stakeholders will be much more influential than an external salesperson in achieving consensus around the decision to purchase a new product or service. Reps should leverage best practices in their team so that everyone knows how to close deals successfully.

 

How do you know when a sales rep is ready to start selling to enterprise clients?

There’s a certain level of care and caution that is needed at the enterprise level. A representative is ready to start selling when they exhibit strong attention to detail, are adept at handling objections on calls, take a high level of ownership and demonstrate the necessary perspective to approach the deal cycle as a “buying journey” from the client-side rather than just a sales process from the vendor.

Building on these skills and characteristics will help sales reps successfully navigate their way through the complex sales process that they’ll find themselves in when selling to enterprise clients. Enterprise selling relies on a sales rep’s attention and customized solutions to close a deal.

Reps also need ownership. The reps who are coming up with excuses instead of self-reflecting on how they can improve and learn from setbacks are unlikely to flourish in enterprise sales.

 

 

 

 

What are the biggest differences that a growth or SMB sales representative will experience when selling to enterprise organizations for the first time?

While there are many differences between SMB and enterprise, most ladder up to a sales rep’s mindset and approach. Enterprise sales is a partnership between the buyer and the seller — there is almost nothing transactional and as a result, deals take longer. If a rep brings a transactional or quick-win mindset to an enterprise sale, they will fail. 

For example, there is far more complexity around managing information, people and processes in an enterprise sale, which requires time and patience. The deals that succeed come from that partnership built with the buyer through consultation and the desire to dig deep.

Another example of how a transactional mindset doesn’t work in enterprise is the reality that funnel metrics tend to trend differently. Many enterprise deals will fail in earlier stages but once something is qualified, the win rate tends to increase. 

If a rep brings a transactional or quick-win mindset to an enterprise sale, they will fail.”

 

How can sales managers prepare sales reps to handle those differences?

Enterprise is a strategy, not a segment. The whole organization needs to be invested in the enterprise strategy from marketing and product to customer success and leadership. Without that, even the most well equipped enterprise sales person will not succeed. A sales manager can assist by preparing a sales rep to utilize these resources to focus their mindset for a more complex environment and give them the runway to take that consultative approach. 

As they prepare to take on a sale that is more marathon and less sprint, it is important to help them adjust to this change. Leaders should remind a sales rep to slow down and strategize their sale. Reps can’t get frustrated when they do not feel like deals are moving as quickly as they are used to. Managers need to get reps to focus on the steps between the steps as each one is its own victory. This will help to keep reps from getting discouraged as they transition to a longer sales cycle. In regard to funnel metrics, reps need to be encouraged to qualify deals out as quickly as possible so they can focus their efforts on the deals with the best chances of closing. 

 

How do you know when a sales rep is ready to start selling to enterprise clients?

The reality is, you never really know and that is okay! Giving a shot at enterprise to sales reps who show the right indicators is the only way to know for sure. What I look for is how they approach a sale — regardless of the size, some reps just lead with curiosity and a real desire to find a solution to the customer problem. 

Another trait that I look for is patience with persistence. As mentioned above, you cannot strong arm a deal through in enterprise and there can be a lot of starts and stops in a deal cycle. I look for someone who will not lose focus or give up when something does not go according to their plan.

 

 

 

 

 

What are the biggest differences that a growth or SMB sales representative will experience when selling to enterprise organizations for the first time?

I think there are three major differences in the sales process for an enterprise customer. First, it’s most likely going to take a lot longer. Not only may large organizations have additional layers of required approvals, but they are also more inherently complex and need to go deeper when signing on a new product or vendor. Second, it takes a greater deal of rigor to understand the customer’s needs. Pain points change both over time and with scale, so knowing the right questions to ask throughout the process is a challenge. Lastly, the biggest difference is the level of ambiguity. We tend to make exceptions or adjustments to accommodate larger clients and with that, we stray from standard processes that keep things easy to follow. I see that ambiguity as exciting! White space is the best place to identify new tactics and processes that can be repeated. 

 

How can sales managers prepare sales reps to handle those differences?

Selling at the enterprise level can be intimidating for sales reps and the rest of the team. Handling the differences between SMB and enterprise sales all comes down to proactive coaching. As a manager, if you can anticipate potential areas of friction — not necessarily the exact problems themselves — you can clearly define these to your sales team so they are prepared to react and adapt. By providing transparency that this might be difficult and there will be roadblocks, reps will be less likely to get discouraged. Additionally, I think reminding everyone that all enterprises started somewhere is important. At the end of the day, we’re selling value to people, not just transferring goods.

Being driven is the flame and being adaptable is the accelerant.”

 

How do you know when a sales rep is ready to start selling to enterprise clients?

When evaluating the performance of members of my team — in sales and other capacities — the key factors I always look for are drive, adaptability and confidence. Digging into the first two together, being driven is the flame and being adaptable is the accelerant. If you work hard at one thing but that one thing doesn’t work, it won’t get you very far. Someone who is able to keep pushing in the face of adversity and know how to adjust their approach or tactics midstream will be able to handle the challenges of selling to large clients. Lastly, I know focusing on confidence can sometimes get a bad rap so what I look for is confident humility, a concept that Adam Grant has done a lot of research and writing on. Someone who has a clear vision of what they want to achieve and knows they may need others to achieve it can handle the twists and turns required to dive into enterprise accounts.

 

 

 

 

What are the biggest differences that a growth or SMB sales representative will experience when selling to enterprise organizations for the first time?

While the goal with both targets is to effectively prospect, qualify and close business with organizations, the biggest difference between SMB and enterprise opportunities is in the timeline, strategy and execution throughout the sales process. Whether it’s smaller transaction sizes within the SMB target market or the fact that SMB organizations tend to be less complex from a process and structure standpoint, an SMB sales representative generally grows more accustomed to a faster, more turnkey sales process and execution. When pivoting to enterprise targets, the sales process timeline will most likely be longer due to more formal decision-making, budget allocation and business need assessment processes within the prospect’s organization. This requires a much more defined approach on the sales representative’s part, in which opportunity qualification and realistic expectation management, both internally and externally, are critical to effective execution.

The biggest difference between SMB and enterprise opportunities is in the timeline, strategy and execution throughout the sales process.”

 

How can sales managers prepare sales reps to handle those differences?

Managers can prepare sales reps to enter the enterprise domain by focusing on key foundational approach points. From an opportunity qualification standpoint, whether a sales organization embraces BANT+, MEDDPIC or some other qualification framework, building a process that leverages opportunity qualification is critical to a successful transition. 

It is also important to use tools such as external and internal account plans to manage expectations with the prospect contacts around elements such as process timeline, budgeting and decision-related transition points, as well as all required operational participation and reviews. This empowers the rep to have a vehicle to refer back to with those contacts, especially when the process may go in unexpected directions or be negatively impacted. Internal account plans enable a sales rep to manage expectations with required support resources, as well as expectations set with sales leadership regarding the size, likelihood and expected close date of an opportunity.

 

How do you know when a sales rep is ready to start selling to enterprise clients?

When they consistently demonstrate all the fundamental sales execution components that position them to best manage the increased complexities that an enterprise opportunity presents. These components include sound opportunity planning, clear process and actionable tools that enable a viable foundation. Additionally, I look for a track record that includes accurate expectation management regarding how many transactions will close and for what dollar amounts, as well as a verifiable history of successfully working through challenging opportunities within SMB. The most critical objective a sales rep entering the enterprise domain should work towards is minimizing the risk that an opportunity won’t successfully close.