Pilot Program: Street Smart Sales Management

STREET SMART SALES MANAGEMENTArrows - Street Smart Sales Management Pilot Program - C Level Strategic - Oliver Connolly

ARE YOU FRUSTRATED BY A SALES FORCE OF UNDERACHIEVERS? Are you ready for a substantial increase in sales and profits? Are you working your tail off but not seeing the results you want? You’re not alone. Many sales managers and vice presidents of sales are so bogged down in the day-to-day busy work, the key stuff doesn’t get done. As a result their sales teams are not performing. Sales are flat or declining.

YOU’RE TIRED OF EXCUSES. You’re fed up listening to the reasons your salespeople are not making their numbers. Sure, the excuses sound legitimate. So what? You want results, not excuses. You’re ready to take action … you’re looking for solutions.

THE BUCK STOPS WITH YOU AS FAR AS SALES ARE CONCERNED.  It’s your job to deliver the numbers the company needs. You can’t settle for the status quo any longer. You’re not alone. That’s why I’m introducing the Street Smart Sales Management Pilot Program. It’s designed to help you build a sales force of consistent overachievers.


  • Struggle - Street Smart Sales Management Pilot Program - C Level Strategic - Oliver ConnollyMARKET SHARE IS FLAT OR DECLINING. In many industries sales volume is not what it was a few years ago. Companies are competing for a piece of a smaller pie. Even where the market has grown there are more competitors. There is less to go around. Competition is fierce. You have to get your share, plus a chunk of the other guy’s share. If you don’t you’re being outsold.
  • THERE IS NOT ENOUGH BUSINESS COMING IN. Your salespeople appear to be busy all the time. They’re taking care of existing customers, putting out fires, spending hours doing “busy work,” and, in general, racking up expenses trying to keep customers happy. Aren’t you tired of hearing them complain about “not having enough time” or “if only there were two of me?” Of course it’s all BS. They have time for everything except prospecting for new business.
  • THE PIPELINE IS BLOATED. The same old opportunities keep showing up week after week but they’ve been stuck in the same place forever. There’s no progress, no change. The reality is they’re not real. They are illusions … nothing more than figments of a salesperson’s happy ears. Until you blow away that house of cards, there will never be any real progress.
  • CUSTOMER ATTRITION. You’re losing customers. According to the Harvard Business Review, companies can boost profits by over 100% by retaining just 5% more of their customers. In the real world, you’re always going to lose a small percent of your customers no matter what you do. Some things are simply out of your control. You do not want to lose customers because of things you did or didn’t do … the stuff you control. It’s hard enough getting new business. You don’t want to lose existing good customers through neglect.
  • YOUR SALESPEOPLE ARE EXPERIENCED. They have years of experience in the industry, tons of product knowledge and great relationships with their accounts. They have the skills and expertise to solve any challenges your clients have. Somehow this is not translating into more business.

WHAT YOU’RE DOING RIGHT NOW IS NOT WORKING FOR YOU. You’re not sure where to start or what to do next to get the results you need

US COMPANIES SPEND OVER $20 BILLION ($20,000,000,000) EVERY YEAR ON SALES TRAINING. Within 90 days, 84% of what was initially learned is lost! It does not have to happen. Most of it is due to a lack of direction and follow-up from sales management.



  • This program is not for everyone. You need to be currently managing salespeople.
  • It is a pilot program. While it is based on tried and true principles of sales management, and on my practical experience over many years in the field coaching and mentoring sales managers, it is not a canned program.
  • The program will be tweaked and developed as it evolves. The core curriculum will be shaped by the input and needs of the participants.
  • Participation will be limited to 20 qualified participants.
  • Results are guaranteed provided you participate to the best of your ability. Do not expect any magic dust or quick fixes.

THE STREET SMART SALES MANAGEMENT PILOT PROGRAM is designed to help sales managers and vice presidents of sales begin building a sales force of consistent overachievers in a relatively quick timeframe. We will work together intensively over a period of several months. Then you will have ongoing support indefinitely, via the sales management forum.

The program will help you:

  1. INCREASE YOUR MARKET SHARE. Just trying to hold on to the business you already have is not enough. You must expand your share. You will learn how to raise the bar for your salespeople, and how to help them achieve it.
  2. ACHIEVE A STEADY STREAM OF NEW BUSINESS. Even the most loyal customers can have set backs. If you are not consistently getting new business, you run the risk of losing ground. You will learn how to set realistic expectations for new business for every salesperson. You will become adept at holding people individually accountable for prospecting and other sales activities. As your business grows, your competitive advantage, buying power and profits will increase.
  3. CREATE AN ACTIVE PIPELINE THAT IS REAL. You need qualified prospects in your pipeline … prospects who need what you sell, and are ready, willing and able to buy from you. You will learn a process to create a solid pipeline for your particular business. You will be comfortable teaching this to your salespeople and holding them accountable for implementing it. They will learn how to cull the non-prospects and focus on opportunities that are real.
  4. COACH YOUR SALESPEOPLE so they become adept at relationship building and customer retention. You will be less vulnerable to losing customers because of low-ball pricing, or aggressive and predatory competitors. You won’t have to worry as much about losing business.In addition you will be better equipped to guide your salespeople’s prospecting activities by helping them with pre-call strategizing and post-call debriefing.
  5. BUILD A SALES TEAM OF OVERACHIEVERS … a sales team that delivers results instead of excuses. Important: This will not happen overnight but it can happen relatively quickly. You must have people on your team who will sell as opposed to people who can sell. There is a huge difference. All the industry experience and sales skills in the world are wasted on salespeople who will not sell.

Airplanes - Street Smart Sales Management Pilot Program - C Level Strategic - Oliver ConnollyWHERE WE START: THE FIRST STEPS

WE BEGIN BY TAKING A LOOK AT WHERE YOU ARE RIGHT NOW. In a one-on-one session we’ll talk about your goals … what you want to accomplish as a sales manager. We’ll look at your sales management philosophies, practices and skills. We’ll talk about what you’re doing well and what you could do better. We will use a sales management assessment to establish a baseline. Together we will build an action plan to get you where you want to go.


  • Your sales management mind set
  • Your sales management skills
  • Setting expectations
  • Tracking activities and behaviors
  • Holding your salespeople accountable
  • Coaching salespeople effectively
  • Training salespeople
  • Knowing when to cut your losses … hiring and firing
  • Much, much more


  • This is not a cookie-cutter program where everyone is fed the same canned solutions. It will be customized to the needs of the group, and in a large part, to your individual needs. The purpose is to help you grow your business.
  • This program is not for everyone. To be accepted you have to be currently managing salespeople. You also have to be willing to actively participate and provide input and feedback.


THE STREET SMART SALES MANAGEMENT PILOT PROGRAM is designed for sales management professionals like sales managers, vice presidents of sales, directors of business development and people who manage sales people or other people responsible for generating sales. The exact title is not important. What really matters is that you manage the people who do the selling.

THIS PILOT PROGRAM INCLUDES 8 GROUP SESSIONS VIA VIDEO CONFERENCE and a minimum of 3 one-on-one coaching sessions with me, Oliver Connolly by phone or video conference.


THE GOAL IS VERY SPECIFIC. Its purpose is to help you generate the sales and profits you need in a relatively short period.

YOU WILL SUCCEED BECAUSE I will show you exactly what it takes to build a sales force of consistent overachievers. I will help you put a complete sales management process into place, and provide you with a high level of support. Even after the initial pilot program you will have access to the bi-weekly sales management forum.

YOU WILL BE PART OF A SUPPORT GROUP OF PEERS … other sales management professionals who have faced the same challenges as you.

THIS PROVEN PROCESS HELPS YOU GET RESULTS FASTER. You will get there with fewer mistakes and less aggravation. You’ll learn what to do, and when and how to do it.

THERE IS NO IVORY TOWER BS. I HAVE BEEN COACHING AND MENTORING SALES MANAGERS FOR MORE THAN 20 YEARS. My expertise comes from the real world … hard earned street smarts as well as classroom learning. I have studied everything I could get my hands on about sales and sales management. I have listened to the gurus and learned from them.

Some lessons I have taken literally, others I have modified to fit my style. I will never recommend something I haven’t tried personally. I have learned from my mistakes so you don’t have to.


Oliver enabled us to identify our organization’s strengths and weaknesses. His programs have had a major positive impact on our results.

John McDonagh, CEO, Publisher

Best program I’ve seen on how to get my sales managers and me on track and keep customers.

Rene Fritz, President/CEO

Practical, down-to-earth programs that work in the real world. A no-nonsense approach to sales and sales management. If you want to take control of your sales organization, you need to call Oliver.

Elizabeth Parke, CEO

I strongly recommend this program to anyone wanting to take the struggle out of managing a sales force in this ever changing marketplace.

Howard Turner, Sales & Marketing Manager


  • THE STREET SMART SALES MANAGEMENT PILOT PROGRAM IS FOR SALES MANAGEMENT PROFESSIONALS … vice presidents of sales, sales managers, and directors of business development or anyone responsible for generating sales through other people.
  • IT IS FOR SEASONED SALES MANAGEMENT PROFESSIONALS who are frustrated by a sales force of underachievers. You need results, not excuses.
  • IT IS FOR NEW SALES MANAGERS who need to get up to speed quickly. It will shorten your learning curve considerably and help you avoid many of the mistakes that new sales managers make.
  • THIS PROGRAM IS FOR MANAGERS WHO WANT TO TAKE THEIR SKILLS TO THE NEXT LEVEL. You’re tired of constantly struggling with yo-yo sales and fighting salespeople just to get them to do their jobs.
  • IT’S ALSO FOR SALES MANAGERS WHO ARE TIRED OF FEELING ALONE in their sales management roles. You don’t want to reinvent the wheel every day. You want a proven process that works. You also want support and validation.

Success - Street Smart Sales Management Pilot Program - C Level Strategic - Oliver ConnollyWHAT WILL HAPPEN IN THE STREET SMART SALES MANAGEMENT PROGRAM?

Initially the program will focus on seven areas essential to building and managing a sales force that consistently overachieves. However, since this is a pilot program, the exact content and sequence may change. There may be tweaks and addendums based on the input and feedback of the participants.

When you take part in this unique sales management program, you will not only sharpen your own skills, you will also help shape the next generation of Street Smart Sales Management Programs.

  • YOU WILL UNDERSTAND AND OWN YOUR ROLE AS A SALES MANAGEMENT PROFESSIONAL. This is very important. Your job is to generate the revenue your company needs, but you have to do it through others. You’re not “one of the boys”. Sales management requires a different mindset and a different set of skills than selling.
  • YOU HAVE TO HAVE THE RIGHT SALES TEAM. As the saying goes, you have to have the horses to pull the wagon up the hill. You have to have salespeople who will sell as opposed to salespeople who can sell. This is critical. All the expertise and skills in the world are wasted on salespeople who won’t sell.
  • YOU’LL LEARN HOW TO SET REALISTIC EXPECTATIONS FOR YOUR SALESPEOPLE. This goes far beyond setting annual quotas. You’ll know how to focus on the activities and the behaviors your people need to be successful.
  • YOU’LL DEVELOP A PROCESS FOR TRACKING. Most managers already track the numbers on a daily or weekly basis. That’s not enough. By the time you see the numbers you’re looking at history. By then it’s too late to correct them. Proactively tracking the activities and behaviors leading to those numbers is essential.
  • YOU’LL MASTER THE ART OF HOLDING YOUR SALESPEOPLE INDIVIDUALLY ACCOUNTABLE. This is one of the most important sales management skills. It’s also an area neglected by many sales managers. Do this consistently and everything else falls into place.
  • WE WILL SPEND A LOT OF TIME MASTERING AND PRACTICING SALES COACHING. You’ll learn how to conduct effective pre-call strategizing and post-call debriefing. You’ll learn what it takes to develop your salespeople … how to help them become better than they are today.
  • YOU WILL SPEND SOME TIME FINE TUNING THE OTHER SALES MANAGEMENT SKILLS AND PROCESSES: General sales management, recruiting, hiring and firing, running powerful sales meetings, territory management, and account management. Some of these will be covered in our individual sessions.

REGARDLESS OF YOUR INDUSTRY, PRODUCT OR SERVICE, or even the number of salespeople you manage, this program will help you increase sales and profits in a relatively short time frame. More important you will develop the skills needed to do it consistently.


I’VE BEEN COACHING AND MENTORING SALES MANAGERS FOR OVER 20 YEARS. I’ve been managing salespeople for much longer. I’ve seen firsthand how important good sales management is to the success of the organization. Unfortunately most sales managers do not get the support or training they need to be successful. Many are tossed in at the deep end of the pool and allowed to sink or swim on their own. Some make it, many don’t. That’s not right! It doesn’t have to be like that.

THE STREET SMART SALES MANAGEMENT PILOT PROGRAM will provide you with the support and coaching you need to implement the skills you are learning. Afterwards you will have free access to the bi-weekly Sales Management Forum. For people who want more long term support and coaching there are a number of options available.

Presentation - Street Smart Sales Management Pilot Program - C Level Strategic - Oliver ConnollyTHE RESULTS YOU CAN EXPECT FROM THE STREET SMART SALES MANAGEMENT PILOT PROGRAM


  • Begin to achieve the sales and profits your company needs.
  • Know how to create a sales force that actually sells.
  • Be confident in your skills to be a successful sales manager.
  • Have mastered a sales management process designed to consistently deliver results, regardless of the type of industry, product or service.
  • Know how to coach salespeople.
  • Be comfortable holding people accountable.
  • Know how to hire and fire … when to cut your losses.


This is a short term but relatively intense program designed for sales management professionals who want to excel. It is for vice presidents of sales, sales managers, sales supervisors, directors of business development and those who are responsible for bringing in business through other people.

During the program you will acquire a process for creating and managing a sales force that consistently overachieves. Afterward the initial stage you will have lifetime free access to the bi-weekly Sales Management Forum.

You will also have the option of signing up for one of my ongoing sales management coaching or mentoring programs. There are several different options and price points depending on your needs.

  • WE’LL BEGIN WITH AN EVALUATION OF YOUR CURRENT SITUATION. We’ll analyze your goals and create a plan to achieve them. We’ll also assess your current strengths and weaknesses. This will serve as a baseline for your growth. This will take place in a one-on-one video meeting with me.
  • WE WILL MEET AS A GROUP EVERY OTHER WEEK. There will be a total of 8 meetings. Each will last between 90 minutes and 2 hours. Each meeting will focus on a specific sales management skill. The meetings will be held every other week so you have time to implement the strategies in the field.
  • YOU WILL ALSO HAVE 2 ADDITIONAL ONE-ON-ONE COACHING SESSIONS WITH ME. We will use these sessions to discuss any challenges you are facing in the area of sales management. Additionally, I will be available by phone or email to answer any questions you may have about the program.
  • THIS IS A PILOT PROGRAM and, as such, may be tweaked or updated according to the needs of the group. I will do my best to insure all participants are a good fit. In that way we can learn from each other. The program is being offered at a significant discount to recognize this input.


If you think this program is for you, please fill out the attached application form. When you submit your application, you’ll be taken to a new page containing the cost and other details.

When I get your application, I’ll review it carefully and we’ll set up a time to talk. I’ll answer all your questions and, if it looks like it’s a fit for you, formally invite you to participate.

I look forward to hearing from you.

Oliver Connolly

Application for Pilot Program: Street Smart Sales Management

Fields marked with an * are required

Please complete the following application as completely as possible. The purpose is to help determine if this program will be a good fit for what you need.

Thanks for completing the application. I’ll contact you as soon as possible and we’ll set up a time to talk.

Oliver Connolly