23 Sales Pros Reveal the Biggest Challenges for Enterprise-Level Sales Professionals (and How to Overcome Them)
Selling for the enterprise is similar to selling for SMBs in many ways, but it also presents some distinct challenges for sales professionals. Selling to the enterprise audience requires gaining an understanding of the multitude of gatekeepers and potential decision-makers that exist, as well as finding ways to overcome barriers and spending the time required to build relationships with each individual along the way. For this reason, enterprise sales cycles may be substantially longer than the SMB sales cycle – possibly even years instead of weeks or months.
Enterprise-level sales executives and professionals must also learn to accept failure (as all sales professionals do) and continuously work against fierce competition, all while working with complex sales cycles that can easily distract from the meaningful, relationship-building aspects of a sales career. Some sales professionals thrive on the enterprise atmosphere, while others are better suited for the SMB arena where they can achieve quick wins and build self-confidence. To find out what challenges today’s enterprise sales professionals must overcome in order to succeed, we asked a panel of enterprise sales professionals and consultants to offer their insights on this question:
“What is the single biggest challenge enterprise level sales professionals struggle with (and how can they overcome it)?”
Read on below to find out what obstacles today’s enterprise-level sales pros are combating and what steps they take to differentiate themselves and succeed in an increasingly tough atmosphere.
Meet Our Panel of Enterprise Sales Pros and Consultants:
Ryan Chan is CEO and Founder at UpKeep Maintenance Management. He is a Chemical Engineer by degree from UC Berkeley and started UpKeep out of passion and frustration by the lack of mobility in today’s maintenance management software. UpKeep has now been deployed to over 10,000 businesses and is a leader in mobile first maintenance management software.
“The biggest challenge for our business doing enterprise sales has been…”
Keeping our contacts, opportunities, and pipeline organized over the course of sales cycles which are sometimes very, very long. A typical sales cycle for our enterprise customers can be anywhere from a few weeks to several months, and we may talk to 5-20 different people in the organization who each have different concerns. Following up at scheduled times and momentum from our initial trial period are some things that can easily be lost. Our team uses Salesforce CRM very diligently to really stay organized, and it has been wonderful!
Jim Herst is the CEO of Perceptive Selling Initiative, Inc., and helps businesses build sales and accelerate cash flow.
“The biggest challenges facing enterprise sales professionals are…”
Salespeople remain mediocre not because they don’t succeed, but because they lack the ability to fail. The ability to fail and continue trying determines success. However, it’s not failure that deters performance; it is rejection or fear of rejection that disturbs.
Overcoming fear of failure can be learned. First realize one’s performance is judged not on the basis of what happens when things are going right, but on what is done right when things are going wrong. Failure and rejection are absorbed as ego threats. Thus, the ability to respond creatively when challenged serves to strengthen personal relationships.
When working with businesses, it is common to find ‘fear of failure’ hiding within sales peoples’ performance. The cure is to recognize and practice reacting creatively when challenged. It can be learned!
Nuno Bernardes, Director of Sales Operations at ForceManager, has a Business School MBA, an MIBM from EAE Business School and a degree in economics from Coimbra and Glasgow universities. He has more than 10 years’ experience working for companies such as Cyñande, Bayer, Capgemini, and Novo Nordisk.
“With the process of globalization, nowadays, sales reps face fierce competition (often without knowing who they are). Under these circumstances, sales professionals struggle to…”
Improve their sales message in order to differentiate and deliver more value than their competitors. The key, in this case, is to improve the quality of each customer interaction and to be more effective on the non-sales tasks, focusing more time on the customer. Technology can be a great help with this, as well as a good collaboration with marketing department.
Terrence has 16 years of experience, in four different cities, with one of the country’s largest 3PLs. Now he’s the Director of Brokerage and Enterprise Sales at FreightCenter where he leads a team of enterprise-level sales professionals in developing relationships with high-volume shippers by providing custom, all encompassing freight shipping and technology solutions and superior service.
“The biggest challenge for enterprise level sales professionals is…”
Staying focused on developing the business relationship. It’s natural for sales reps think of sales on a transactional basis, especially when faced with monthly quotas. But, enterprise level sales is about developing longer-term relationships – relationships that are based on trust and commitment and deliver sustainable results for your clients.
To overcome this challenge, enterprise sales professionals must have a sales process and follow it. Within that process, include discovery techniques for asking questions that uncover needs and create a demand for your services. Take the information you learn and tell the story of how the value of your services will support the needs of your client and their customers. When you discover how to make your customers’ customers happy, you will win and grow more enterprise client accounts.
Karen is a business and technology writer and researcher who specializes in sales management and HR. She is currently editor of the GetApp blog, and has previously covered everything from mobile app reviews, to B2B topics for retail and manufacturing.
“Salespeople are struggling with cumbersome sales processes, which are…”
Preventing them from generating leads. Process for process sake doesn’t make sense in the sales world, and these processes need improvement if enterprise level sales professionals are to generate more leads. This issue is exasperated by spending too much time calling and emailing leads — in fact, 60% of companies with active sales reps spend a minimum of 20 hours per month (per rep), selling via email or over the phone, and 26% spend in excess of 60 hours each month calling and emailing. In addition, this challenge is furthered by the fact that sales reps don’t have enough insight about their potential customers to be able to contact them on the right channels. Sales professionals often still favor using phone, email or in person visits, rather than contacting clients in newer channels such as social media. Both LinkedIn and Twitter are useful tools that can improve lead generation.
To overcome this challenge, enterprise sales professionals need robust sales management tools to help them streamline their processes, automate time-consuming manual tasks, and gain better insight into their customer to enable them to contact them in the channel they desire. These tools can also help sales professionals better manage their pipeline, analyze past interactions to better forecast future transactions, and automatically produce reports with important tracking metrics to ensure goals are met.
Brian W. Sullivan
Brian W. Sullivan is co-author of SANDLER ENTERPRISE SELLING: Winning, Growing, And Retaining Major Accounts (McGraw-Hill / 2016). Sullivan is Vice President of Sandler Enterprise Selling at Sandler Training.
“There are several significant challenges that sales representatives and sales teams face in selling into complex enterprise accounts…”
One of the most daunting is that enterprise sales cycles can be long and drawn out. Months, and even years, can pass while pursuing an opportunity with an enterprise organization. And as the time passes, the doubt, uncertainty, risks, and costs add up. And this draining of resources goes beyond the financial. The human assets applied to an enterprise pursuit and the overall energy of the selling organization are also casualties over time.
So, how do selling organizations overcome these frustrating challenges? First, you must follow an effective territory, account and opportunity planning process that maximizes the likelihood that the deals you pursue are the ones you’re most likely to win. And having such an intuitive process that maps what you do best to the opportunities you’re considering pursuing also acts as your guide to insure that you don’t embark on the deals that don’t match your profile.
It sounds simple, doesn’t it? Clearly understanding what you do well and not so well and using that knowledge to create the best matches possible in the deals you pursue. But such fundamental planning is often ignored. Or pushed aside by emotional attachment to tantalizing deals that should never be considered.
And once you’ve done that effective planning, that due diligence to increase your odds of winning, what can you do over that long sales cycle to improve your chances of success? As the time passes, every action you take is being evaluated by the buying organization – actions that showcase your responsiveness, follow-up, and attention to detail. Or lack thereof. Leaving the buying organization with positive impressions in these areas is critical. Because regardless of how capable, prepared and sophisticated your competitors are in the pursuit, they might become just a bit forgetful as the long months go by. They might take their eyes off the ball for just a moment. Perhaps they’ll completely miss a deadline or carelessly provide the prospect a boilerplate response instead of devoting the required time and effort to respond in a customized way. At just the right time to leave just the wrong impression.
The key is to stay focused. With effective territory, account and opportunity planning, trust in your due diligence. And with your process establishing the deal as well worth pursuing, make sure your actions clearly illustrate that the deal is worth pursuing well.
Dan Weinfurter is the Founder and CEO of Chicago based GrowthPlay. GrowthPlay is focused on helping companies drive profitable revenue growth by improving overall sales effectiveness. GrowthPlay addresses a pressing market need to help businesses achieve better results by improving the capability and performance of front line and customer facing staff.
“The single biggest challenge for the enterprise sales rep is…”
Spending too much time not selling. (Cumbersome processes, administrative burdens, etc… pull reps away from actually selling.). If your sales organization spent more time selling, how would that affect your sales revenue numbers? Often, salespeople and front-line managers get bogged down in forecasts, reviews, hiring, and recruiting. In fact, McKinsey Global reports that salespeople spend less than half their day selling.
One of the most common sales challenges for leaders is ensuring that their sales team is spending their time where they should be – building and converting pipeline into deals. Here are four ways you can keep your sales team focused on selling.
1. Provide Sales Consumable Information
If your team has to spend an unreasonable amount of time thumbing through stacks of sales scripts and spreadsheets in order to track and measure results every step of the way, you’re only helping one side of the sales equation.
The other side of the equation is making it easy for them to do their job. This means providing them with sales consumable information that they can access and execute with their prospects and customers. The tools they use in their sales planning and execution processes should be practical and repeatable. If you don’t have a mechanism that enables your sales team to drive efficient pipeline, forecast accurately and effectively move opportunities through the sales process, you can guarantee your team will spend more time with organizational logistics than with their opportunities and customers.
2. Provide Your Frontline Managers With Streamlined Processes
By helping your front-line managers execute their job efficiently, you free them up to spend more of their time coaching their sellers to sell.
Provide your frontline managers with a structured Management Operating Rhythm® in order to keep them focused on specific high-level sales activities. Think of the Management Operating Rhythm as a sales cadence – an intentionally repeatable process to guide their strategy and execution.
When built around consistent messaging and goals, a solid operating rhythm allows your front-line managers and sellers to begin speaking the same language and helps everyone get clear on the benchmarks needed to be successful. The result is that your managers are less burdened and your sellers have space to be coached to success.
3. Provide Structured Feedback
Having a structured feedback and review process is essential to the growth and success of your sales team. It builds a relationship of trust between your managers and sellers, and it allows you to measure whether or not your desired best practices are being executed. Putting a process around giving feedback helps ensure your salespeople continue to focus on the key activities that drive sales.
Give productive feedback by starting out with the positive. Offer your sellers some insight into the things they’re doing right. A little positive reinforcement goes a long way to shaping the right kind of behaviors.
Then, ask your seller what he/she thinks. You can ask questions about a specific sale, project, or even general work situations. Provide the opportunity for them too voice their opinions on how they view their progress.
Next, it’s time for you to provide them with feedback. Make sure that the feedback is specific, measurable, achievable, realistic, and timely. General feedback is difficult for people to put into action. So if you want actionable results, you have to provide actionable feedback.
Finally, make sure that you’re modeling the right way of doing things at the leadership level. Sellers will try to emulate leadership, even if they aren’t aware of it. If you’re not modeling the right kind of behavior, you likely won’t receive the right kind of behavior.
4. Provide Them With The “How”
Good sales leaders clearly tell their sellers what result they should aim to achieve. Great sales leaders show them how to get there.
It’s great to be able to stand up in a sales training and inspire your sellers to hit the next quota in record time. But unless you can provide them with an actionable process to make that happen, you’re setting them up for failure. As a sales leader, your job is to ensure that you help your sellers achieve the results you ask for.
Similarly, it’s important that you have a reason for every result you ask them to achieve. Countless sales leaders ask for reports and forecast reviews and never put them to use. This often happens simply because, “It’s just the way we’ve always done it.”
If you ask your sales managers for a report, let them know why it’s important and how you plan to use it. If you ask your sellers to hit a certain quota, let them know how the number serves the overall business goals, and that it’s not just an arbitrary number.
Your sales team will surprise and delight you when you clearly define what is required of them, why it’s important, and give them the tools to do their job the right way.
David is an Enterprise Account Executive Recruiter at Betts Recruiting. Before joining Betts Recruiting, David was an RFP Associate and Account Executive at Fisher Investments. He graduated from the University of California, Davis with a Bachelor’s degree in Economics.
“I have seen many enterprise sales representatives struggle with…”
Changing industries or departments they work in. This is one of the biggest challenges of having a focused experience. At the enterprise level, many companies look for candidates with very specific types of backgrounds with a product or type of prospect. Representatives can overcome this challenge, though, by creating as many parallels as possible in their current positions and background with the requirements of a new role. An example would be if a representative has spent the majority of their career selling into human resources, and they want to move into marketing, they can position their success as navigating complex deals and how they work within a team. This is where a recruiter can be extremely helpful in explaining their story to a hiring manager.
Joey is an Enterprise Sales Recruiter at Betts Recruiting. Prior to Enterprise Sales, Joey also was an Account Executive at Betts. Before joining Betts Recruiting, Joey was an Area Sales Manager at 21st Amendment Brewery Cafe. He graduated from the University of Colorado at Boulder with a Bachelor’s degree in History.
“The biggest challenge I have observed enterprise sales people face while making a move from one position to the next is…”
Finding a company, role, and leadership structure that fits their skill level and offers an opportunity to be as successful as they are currently. Lots of enterprise sales representatives have built a book of business and an established skill set that they want to bring with them to their next role, but it can be challenging to find a role that allows this. To overcome this, enterprise sales representatives can work strategically and deliberately through the interview process to qualify their opportunities just as they would a sales prospect. Applying the same methodology to their own personal opportunities can ensure that when a job offer comes, they know whether or not the new role will allow them to dive right in and be up to speed in no time.
Keith Johnstone is Marketing Manager of Peak Sales Recruiting, a leading B2B sales recruiting company launched in 2006. As Marketing Manager, Keith leads all marketing activities and has successfully grown revenue and lead volume every quarter. He plays a key role in driving Peak Sales Recruiting which leads the industry with a success rate 50% higher than the industry average. Keith is an expert on B2B sales and recruiting matters, and is a regular contributor to the Peak Sales Blog and @Peak Executive Newsletter.
“The single biggest challenge enterprise level sales professionals struggle with is…”
Their ability to meet quota. On average, only about 40% to 65% of reps will achieve their quota, and even less will consistently achieve quota, year-over-year.
“A big challenge for enterprise sales professionals is…”
Understanding the nature of risk in a larger enterprise organization. Not just for the enterprise, but for the individuals involved. What is the risk to the primary decision maker? He or she won’t want to make a risky decision that will negatively impact their career trajectory. People don’t usually want to put their necks on the line. If you can make that decision less risky, you have a much better chance of making the sale.
It’s difficult to make a decision less risky for an individual. The best way to do it is to dilute the decision-making process by ensuring you have multiple stakeholders at the client side involved with the decision – and you as the seller need to encourage this and get them involved early on. This means you need to proactively engage with other team/business members so that there is less risk for any one person.
This sometimes goes against your instincts – you believe that more people involved with the decision making process makes getting a decision tougher. But where there is risk, you have to spread it around.
Drew Stevens is an international best selling author of two sales books and has written over 900 articles on sales and customer service. He is the founder of two accredited sales programs and is frequently requested by the media.
“The single biggest challenge that enterprise-level sales professionals are facing is…”
Getting through to the buyer. Over 93% of enterprise selling professionals get caught in bureaucracy or allow subordinates to control the buying experience. The best selling representatives know how to network and save time by meeting only with the buyer.
Jake Dunlap is the CEO of Skaled, which he founded in 2013. A top-level sales leader and entrepreneur with deep experience leading high-performing sales and operational functions for global organizations and startups, he specializes in developing repeatable, sustainable processes. Since hiring Skaled as their scaling partner, his clients have raised over $250 million.
“One of the biggest challenges enterprise-level sales pros face today is…”
When closing enterprise deals, the way you set up the initial proof of concept (pilot) is critical for enabling you to quickly get to the largest deal. The process for most companies is unstructured and it takes three years – versus 18 months – to get from step one to the big win.
Matthew DiGeronimo is the General Manager for Veolia Energy North America. With a background in nuclear, coal, natural gas, and biomass/gas power plants, in addition to water treatment and wastewater treatment facilities, Matthew oversees operations and business development efforts. A retired Naval Nuclear Submarine Lieutenant Commander, Matthew also has experience in Mergers & Acquisitions, commercial real estate, and construction.
“Enterprise-level sales professionals often run into the issue of…”
Listening more than talking. Your prospective clients need to like you before they will buy from you. Everyone likes a listen better than a motor mouth. Additionally, there is no better way to announce that you are new to sales than by running off at the mouth. The best sales professionals learn to listen more than they speak. Overcome this by:
1. Practice being comfortable with silence. When there is a break in a conversation, practice not being the one the fill the silence with a response.
2. Take notes. If you are tempted to talk immediately following something your potential client has said, take notes instead. As you do this, 9 out of 10 times, the prospective client will break the silence and introduce more information to you.
Thomas Ngo is the sales manager for Innovative Comfort Systems, which provides HVAC, Mechanical, and Refrigeration services.
“One common challenge for enterprise sales representatives is…”
The best thing I can say is: don’t have a plan B. Most sales professionals got into sales because something else didn’t work out the way they wanted, layoff, etc… getting into sales as a stepping stone is the biggest mistake. No surgeon operates on the premise of a ‘stepping stone’ or ‘let’s try this.’ If you determine this is it, you will invent ways that work for you to the top. Most books on sales are techniques that work for others, but those successful people first that had the determination that this is it for them, and there’s no plan B. If you have the same attitude, you’ll develop the techniques that work only for you, and will be teaching that to employees in no time.
Oleg Smirnov has been a sales manager for international data backup and recovery software corporations for 15 years. It is crucial that he believes in channel sales, and he spends most of my time building up relationships and reputation in the market. Prior to Paragon Software Group, he worked for Veeam as a BDM responsible for the Middle East region.
“One key challenge faced by enterprise-level sales reps is…”
To work in sales for enterprises is, to some extent, easier than for the other (i.e., SMB) market segments because big enterprises tend to hire highly skilled professionals. So, if you have the right product, and you are capable of providing all the information in the correct way, the technical side of the matter will work out just fine and there will be no need to educate your customer a lot on the subject. They are eager and able to clearly specify the problems they need to solve within their organization. However, the main challenge is that the infrastructure within big enterprises can be quite complicated with long decision-making chains and multiple levels of management. You need to find out who you need to talk to (and it is not going to be just one person) in addition to all of the other steps in the purchasing process that you have to take. It turns out to be one of the most challenging parts of the game, especially in the top enterprise segment.
Sheila Lindner is President of Canada’s foremost provider of high quality document management and business process outsourcing solutions, Octacom. Octacom provides a wide range of customized solutions for large, international enterprises.
“The most important thing for enterprise-level sales pros to understand and remember is…”
Sales to enterprise-level businesses requires a different and often more sophisticated approach than traditional sales. In the enterprise space, the buyer network is much more complex – wider and more diverse than you generally encounter within traditional sales interactions. Effective enterprise sales requires a unique approach that will accomplish the various goals of the enterprise, balancing different interests and appealing to the objectives of competing departments.
John Knotwell is the Chief Revenue Officer at RizePoint – a corporate compliance SaaS company based in Utah. As CRO, John is responsible for leading Worldwide Sales, Channels, Services, and Customer Success. Prior to RizePoint, he was VP, Sales at Workfront Inc. where he was instrumental in achieving an average of 50% YoY revenue growth for 3 years running. Prior to Workfront, John was VP of Sales at inContact (NASDAQ: SAAS).
“The biggest challenge facing enterprise sales reps in 2016 is to…”
Provide commercial insights to their prospective customers, which differentiates value and reduces commodization of their product. The buying process has changed dramatically in the last decade. According to research from the Corporate Executive Board, 57% of a buyers decision has been formulated before they ever contact a sales person. That means that more than half of the criteria used to determine a fit for a solution has been ingrained and, potentially, assumed. As such, enterprise sales executives must deconstruct the buyer’s assumptions and reconstruct them into a new paradigm that aligns the goals of the purchase with the product the sales person is selling.
Commercial insight is not always easy to find. Enterprise organizations are complex with myriad initiatives, personalities and politics. At the same time, sales reps are making decisions about how much time to invest in each target account. Successful organizations acknowledge those complexities and enable the sales person with tools to showcase market awareness, progressive industry trends and innovative approaches to solving problems within the buyer’s journey. These tools, combined with swagger and determination on behalf of the sales professional are keys to a successful interaction with a future client.
Barbara Weaver Smith
Barbara Weaver Smith is founder and CEO of The Whale Hunters, helping companies grow by making bigger sales to bigger customers. She is author of the new Whale Hunting with Global Accounts: Four Critical Sales Strategies to Win Global Customers and co-author of Whale Hunting: How to Land Big Sales and Transform Your Company.
“Enterprise sales professionals struggle with…”
Knowledge. They need to know about the prospect, the influencers, the industry, the market, the competition (theirs and their prospect’s); they need business acumen; they need to know how to manage an 18-month or longer sales journey and to be in the leadership role; they need to know enough to craft a powerful vision for their buyers of what’s possible to achieve. Most important, they need to know enough to have such good conversations that executives invite them back!
They can overcome the knowledge challenge by curiosity:
- Collect all the information you can find about the breadth and depth of the company’s interests, operations, and plans
- Read/listen/watch highlights of trends in science, technology, economics or other “non-sales” topics
- Get your team or another group involved in “what if” talks about how seemingly unrelated trends or ideas might impact your company, your customers, or your competitors
P.S. This should be Job 1 for your sales enablement team!
Ike Jablon is a Senior Media Relations Specialist for GetApp™.
“After surveying 250 sales professionals on their biggest challenges and how they overcame them, here are some key findings from a recently released report…”
The key challenges faced by enterprise sales pros include:
- Only 10% of sales reps believe shoppers are looking for personalized customer service.
- Right now, just 15% utilize social to connect with their potential customers.
- Exactly two-thirds admit their sales process needs lead gen improvement.
- 34% of all sales reps still haven’t adopted any kind of sales software.
In terms of how to overcome these challenges, we found that adopting sales software is the most critical element. After sales professionals adopted sales software: 95% increased productivity, 86% boosted revenue & 78% improved customer satisfaction.
Carol Margolis is a business travel expert boosting traveler safety and productivity. She is the author of Business Travel Success: How to Reduce Stress, Be More Productive and Travel with Confidence and is a frequent TV and radio guest, appearing on Good Morning America, CNN, Fox, USA Today, New York Times, and more.
“The biggest challenge for enterprise-level sales reps is…”
Sales professionals struggle with the challenges of business travel – whether driving or flying. Reaching sales quotas and having a home life while traveling to prospective and current clients is a challenge not often talked about. As a 30-year road warrior traveling throughout the U.S. and the globe, recommendations for overcoming these travel challenges include:
- Have checklists for both packing and re-packing (so as not to leave anything behind in a hotel), which helps with organization and also reduces stress.
- Have expense apps that make it easy to scan and record expenses so this admin task isn’t left for precious home time.
- Make it a priority to get some fitness in each day, even if it’s just 20 minutes inside your hotel room. This helps create more energy and reduces stress.
- Ask a hotel for a “shut down call” at a reasonable time in the evening (a reverse wake-up call that prompts you to shut down your ‘work’ mode).
Dev Tandon is the Founder and CEO of The Kini Group, which provides cloud-based business analytics software that drives powerful and intuitive margin analysis. The technology allows companies better to identify critical issues and opportunities related to sales performance, mix data, customer churn, price realization, and more.
“Enterprise sales professionals have one great advantage…”
A wealth of customer and product data within reach. Unfortunately, this is also their biggest challenge. They often drown in unorganized data, unable to find the actionable insights they need to improve their sales strategies. They lack an intuitive and robust analytics tools that can keep up with their pace of business.
AJ Saleem is the Director of Suprex Private Tutoring, a leading private tutoring and test prep company based in Houston. AJ has created a big dent in the private tutoring market by offering well-trained, high qualified teachers who are also dynamic instructors. The company also operates in New York and Chicago.
“Sales is a big part of my company, and our biggest challenge is…”
Client interest. My business provides an important service for society, but many people do not realize it. As a tutoring company, I need to find interested potential clients in order to sell tutoring packages. What I have learned is that if you let your passion shine through, then you are better off.
AN ALTERNATIVE GUIDE TO SALES KICKOFF
HOW SALES CONTENT MANAGEMENT CAN HELP YOUR COMPANY
REPS SPENDING ONLY 32% OF THEIR TIME SELLING
Further Reading from the Docurated Blog:
- What is Agile Marketing?
- B2B Marketing Automation Tips
- 10 Components of a Marketing Plan
- Top Marketing Automation Tools
- Measure Marketing ROI
- Strategic Marketing Plan Resources
- Account Based Marketing Resources
- Consultative Selling Tips
- Sales Pipeline Management Tools
- Business Analytics Software
- Digital Marketing Trends