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IT Sales Strategy and Selling to the CIO Sales Training Workshop

Steve Martin’s IT Sales Training has helped over one hundred fifty high technology companies improve their sales effectiveness. In addition, Steve has interviewed hundreds of CIOs, CTOs, VPs (eCommerce, Operations, Applications), and countless mid and lower-level IT personnel as part of the win-loss studies he has performed for companies including IBM, EMC, ATT, Acxiom, and PayPal. Steve is also a Silicon Valley sales veteran with nearly two decades of software sales experience.

The IT Sales Strategy workshop is completely customized to your unique sales situation and specific areas of need. To ensure topical relevance, extensive pre-session interviews and background research is conducted to understand your marketspace, competitive position, products, and salespeople. Workshops are designed to address your critical sales challenges and use the terms and nomenclature of your products, company, and vertical industry. Workshops vary from half-day to one or two full days in length.

The training is completely interactive and incorporates extensive exercises/role-playing to apply the concepts on active accounts or immediately on the next sales call. Everyone can ask tough questions, share their experiences, work on their weaknesses, and learn entirely new skill-sets. Learning by example is the best way to learn and the workshop includes best practices of other technology companies. Finally, Life’s too short not to have fun and humor plays an important role in every workshop to keep sales teams (salespeople, inside sales, system engineers, and consultants) engaged and the atmosphere upbeat.

Heavy Hitter I.T. Sales Strategy

Heavy Hitter I.T. Sales Strategy is a comprehensive guide for penetrating new accounts, differentiating your solution during the sales cycle, and winning highly competitive accounts. It is based on extensive research and interviews with more than 1,000 key information technology decision makers, top technology salespeople, and vice presidents of sales. The book provides state of the art technology sales strategies and advanced tactics for senior salespeople who want to learn the secrets of top performers. There are five sections:

  1. Technology Sales Organization Strategy: Key Trends and Performance Metrics
  2. Advanced Sales Cycle Strategy: Control the Complex Technology Sale
  3. Sales Call Strategy: Strategically Structure Meetings to Differentiate Yourself During Customer Meetings
  4. New Account Penetration Strategy: Language-based Tactics to Secure Initial Customer Meetings
  5. Personal Communication Strategy: How to say the Right Words at the Right Time to Convince Customers to Buy

Readers will find advice on how to win over C-level I.T. executives and senior business leaders across the organization. Discover how I.T. organizational structure impacts company decision making. Determine how to gain strategic account control based upon the people, process, and politics of selling to complex businesses. Learn to conduct persuasive sales calls using sales linguistics, the study of how the customer's mind uses and interprets language. The book is written using an easy-to-read format with extensive examples, illustrations, and practical case studies.


"For senior executives seeking to validate their strategy, mid-level managers to better guide their organization, and front line salespeople who must execute their sales call agenda."
- Sam Levy NetSuite, Vice President of Sales, NetSuite

"Communicates complex concepts and relevant insights in a way that makes sense to salespeople."
- Dave Carter, Senior Vice President of Sales, CornerstoneOnDemand

"Learn the strategies Heavy Hitters use that distinguish them from average salespeople."
- Eric Entzeroth, Senior Vice President Global and Strategic Accounts, Genesys

"Without great salespeople the world's most sophisticated forecasting methodology will only tell you that you're not going to make your number and it will be right."
- Mike Munoz, Vice President of Worldwide Sales, Nimble Storage

"The interviews magnify the need for salespeople to understand how and why customers buy."
- Tony Cassetta, Head of Business Performance and Transformation, Nokia Networks

"Read this book in a hurry! Bookmark and keep it on your desk for future in a reference."
- Elango Rathinavelu, Executive Vice President, Mphasis, a Hewlett Packard Company

"Insightful, inspiring, and will give you an edge in the changing dynamics of selling today."
- Joe Vitalone, President of Americas, Mitel

"Invaluable tips that are a must-read for anyone looking to succeed in technology sales."
- John Reese, Senior Vice President of Marketing and Sales Development, Velocify

"Practical Insights that can be incorporated into any sales methodology an organization uses."
- Dan Leary, Vice President of Sales, CSG Systems International

"The reader feels like a participant in a forum between a diverse array of successful sales VPs."
- Mac McGary, Executive Vice President of Global Sales, GT Nexus
"Techniques and insights based on thousands of interviews with both hi-tech buyers and sellers."
--Henry Schuck, Chief Executive Officer, DiscoverOrg

"Skillfully and succinctly covers the strategic sales process where sales professionals can grow the most."
- Stephen Xeller, Senior Vice President of Major Account Sales, Perceptive Software

"Compelling research, insightful observations, and the recommended tactics are differentiating."
- Rob Consoli, Senior Vice President of Mid-Market Sales, Liaison Technologies


  • How technology decision makers think, evaluate vendors, and select the winner.
  • Comprehensive strategies for winning different types of hi-tech sales cycles.
  • Key moments and turning points during sales cycles when deals are won or lost.
  • Tips, techniques and best practices of top technology salespeople.
  • How I.T. organizational structure impacts the vendor selection process.
  • How to conduct persuasive sales calls based on technology buyer personas.
  • Strategies to maintain account control and establish situational dominance.
  • How and when to use provocation versus alignment during sales cycles.
  • Understand the IT budgeting process and the impact of procurement.
  • Facts and metrics regarding customers' price sensitivity and decision influence.
  • How top technology salespeople are using social media such as LinkedIn.
  • How to write persuasive e-mails to penetrate new accounts and secure initial customer meetings.
  • How to build unbeatable customer relationships using sales linguistics, the study of how the customer's mind uses language.


  • Top technology sales organization trends and best practices.
  • Optimum sales organization structure based on product type and stage of company.
  • What separates great from good technology sales organizations.
  • Compare your management style against your peers.
  • Key performance indicators and metrics to measure your organization's performance.
  • Sales cycle strategy best practices to better guide your sales organization.
  • How to coach salespeople to sell business solutions across the company.
  • Top reasons technology salespeople lose business.
  • Quota assignment, on target earnings and what percentage of salespeople achieve quota.
  • Direct, channel, inside, and SMB sales force composition measurements.
  • Personality traits of top technology salespeople for more effective hiring.
  • Expert advice on how to gain strategic account control based upon the people, process, and politics of selling to complex accounts.
  • Comprehensive sales call strategies to improve sales team effectiveness.

Part I - Enterprise IT Sales Strategy
The grand strategy to win the complex IT sale is based upon influencing the people, selection process, and politics of customer decision making. In enterprise accounts, salespeople must penetrate large organizations, influence key decision makers, and dovetail their products' benefits to customers' internal politics. In order to win, they must build relationships with buyers in different departments all across a company. They have to persuade people to believe in their solution at all levels of the IT organization and compete against competitors with similar products and equal sales acumen. The winning IT sales strategy is a psychological operation that is built on understanding, predicting, and influencing human nature. The victor understands how the account is organized and anticipates how the key decision makers will make their buying decision. Moreover, the winner employs a linguistic strategy that enables his message to rise above all others, a tactical plan of execution, and impactful recommendations that compel decision makers to take action. Topics covered include:

  • Formulating the Grand Strategy to Win the Complex IT Sale
  • Political Account Structure of IT and the Psychology of IT Organizational Buying
  • Tactics to Defeat the Competition
  • How Start-ups can Defeat Gorillas
  • Winning Over Key Decision Makers at all Levels of IT
  • Understanding the Political Structure of the Account
  • Determining Departmental Buying Types
  • Translating the Grand Strategy to Tactics
  • Assessing Account Position
  • Account Maneuvers to Improve Competitive Position
  • Win-Loss Analysis: The Seven Premises of the Complex IT Sales Cycle
  • Survival, Successful, and Significant Customers
  • Categories of IT Buyers
  • Should We Pursue the Deal?
  • Identifying and Bonding with the Bully with the Juice
  • Strategies to Find and develop Internal Champions and Coaches

Part II - Selling to the CIO
Every salesperson claims their product will help the customer save money, become more profitable, or improve efficiency. As a result, these claims are seldom believed and very rarely acted upon by senior executives. Today, it takes a comprehensive strategy to winover the CIO. A strategy that enables a salesperson to differentiate himself from the competitors through value. Topics Covered include:

  • The Grand Strategy to Winover the CIO
  • The Four Different Types of Departmental Buying Types (Consolidators, Consulters, Responders, and Bureaucrats)
  • Penetrating the Organization at Various Levels of Responsibility
  • Navigating to the CIO: Top Down and Bottom Up Approaches
  • Maneuvers and Tactics to Defeat Arch-enemies
  • Flanking Strategies When You're Stuck at the Wrong Level
  • The Human Nature of the CIO: A Personal and Psychological Profile
  • Selling the Four Values of Your Solution: Strategic, Operational, Political, and Psychological
  • Presenting Your Solution: Using Logical Arguments, Emotional Appeal, and your Character
  • Organizing the Presentation to the CIO: How to Gain Credibility, Overcome Objections, and Consensus
  • Connecting with The CIO through Sales Linguistics(Using the Right Words at the Right Time to Persuade the CIO to Buy)

Part 3 - Advanced IT Sales Call Strategy
The salesperson's most important competitive weapon is his mouth, and the winner is the salesperson who uses words that reduce the customer's doubt, eases his fear, and fosters his fantasy. That's why it is critical that salespeople master sales linguistics, the study of how the customer's mind uses and interprets language. Customer inertia, the drive to "do nothing," far outweigh the logical reasons you espouse for buying your product. You can recite a litany of reasons and a laundry list of benefits, and the customer still won't buy. This session will equip salespeople with linguistic strategies to differentiate their technology solution from the competition and enable them to create a call to action that convinces business and technical evaluators mentally and emotionally to buy. All competent salespeople can recite their products' features and specifications. Great technology salespeople build winning customer relationships based upon establishing rapport. In this session we review how to speak the customer's language and understand individual needs in order to execute winning sales calls. Topics include:

  • Sales Call Strategy and Stages
  • Sales Call Planning, Structure, and Communication Themes
  • Sales Call Execution: Conducting Persuasive Sales and Calls Presentations
  • Communicating Strategic, Operational, Political, and Psychological Value
  • The Persuasive Elevator Pitch: Linguistics Structure and Compelling Delivery
  • Messaging to the Customer's Mind via Letters, Emails, Phone Calls
  • Understanding and Anticipating Your Customers' Thought Process
  • Mastering Account Qualification during Face-to-Face Meetings
  • Objection Handling using Offensive and Defensive Call Statements
  • Customer Sales Call Coping Mechanisms
  • Psycholinguistic Differentiation Techniques
  • Group Presentation Strategies and Tactics
  • Closing Strategies and Advanced Linguistic Tactics
  • Sales Call Segmentation using Sales Linguistics
  • Personal Persuasion and Establishing Dominance
  • Positioning and Executing Demonstrations
  • Evaluation and Proof of Concept Strategy
  • Controlling Pilots and Proof of Concepts
  • IT Negotiation Strategy: Closing Strategies and Negotiation Tactics

Part 4 -Tales From The Field: Interview Session with Your Top Salespeople
A key element of IT Sales Strategy workshop is the “Tales from the Field” top salesperson panel. "Tales from the Field" is similar to a roundtable talk show where your top salespeople are interviewed about their major wins and losses. However, this session goes far beyond discussing sales strategies and tactics. The psychological and intuitive aspects of selling are translated into common themes and models the entire sales organization can understand and emulate. The sharing of this "collective intuition" stops salespeople from chasing bad deals, helps create a more predictable forecast, and gives each participant (from novice to expert) tactics they can use immediately.

Sample Workshop Outline

1. IT Sales Strategy
  a.Different Types of Grand Strategies
    i.Indirect Approach versus Direct Approach
ii.Examples from other Relevant Technology Companies
iii.Exercise – Application to Accounts
  b.IT Sales Cycle Process
    i.Types – Existing, Persuasion, Creation
      1.Results from Win-Loss Analysis Studies
    ii.Exercise – Application on Accounts
  c.IT Organizational Power and Political Clout
    i.Understanding IT’s Role in the Organization
ii.Bully With the Juice & Emperor
  d.Deal Qualification
    i.Business/Technical/Company Criteria
ii.Privileged Intelligence & Accurate Information
iii.Developing and Categorizing Internal Advocates
2. IT Organizational Structure and Sales Psychology
  a.Understanding IT Structure and Organization
b.IT Budgeting Process Review
c.Strategic, Operational, Political, Psychological Value Statements
  d.IT Departmental Buying Type
    i.Consolidators, Consulters, Responders, Bureaucrats
3. IT Department Account Penetration
  a.Top Down and Bottom Up Strategies
  b.Building the Pipeline
    i.“1, 2, 3, Rest, Repeat” Campaign
      1.Examples from other Technology companies
  c.The Persuasive Elevator Pitch
    i.Structure and Examples
  d.Cold Call Script Review
4. Selling to the CIO Using Sales Linguistics
  a.Seven Types of Languages CIOs Speak
    i.Personal Connection Languages
      1.High Technology Examples
    ii.Logic and Psychological Appeal Languages
      1.High Technology Examples
  b. Understanding Business Operations impact on IT
c. Building Rapport with Sales linguistics
ii.Exercises and Personal Testing
5. Sales Call Strategy
  a.Sales Call Themes
b.Sales Call Stages
c.Sales Stage Strategies
d.Structuring Presentations
e.Positioning and Executing Demonstrations
f.Evaluation and Proof of Concept Strategy
    i.Controlling the Pilot
  g.IT Negotiation Strategy
h.Closing Strategies
i.Negotiation Tactics
6. IT Salesperson Personality Test
  a.Personality Measurement Introduction
b.Metrics and Results
c.Test Administration (~20 minutes)
d.Results Compared to Study of 1,000 Top Technology Salespeople
e.Selling Style Impact Discussion
7. Top Salesperson “Tales From the Field” Interview Panel

Training Session Based Upon “Win-Loss-No Decision Sales Cycle Study”
Since the complex nature of the IT sales process requires huge investments of resources (manpower, time, and money), it is critical to know the circumstances surrounding wins and even more important, losses and no decision sales cycles. True win-loss analysis that is based upon extensive customer interviewing is the best way to understand the political, organizational, and technical aspects of prospective customers' decision-making process. This commissioned study provides the point of view from your prospective customers delivered via a custom workshop to help you understand why you aren't selling more. See the Win-Loss Analysis page for further information.

This valuable information is presented at your sales meeting along with recommendations to improve new win competitiveness. The price for the win/loss study will vary based upon the scope of research and number of customer interviews.