Great positioning drives great results.

GiantLeap helps B2B technology teams develop breakthrough positioning strategy, aligning marketing and sales to achieve faster growth.

We deliver positioning stories, messaging platforms and sales enablement toolkits that trigger buyer interest, spur investigation, and establish a foundation for sales success.

By developing the right story the right way, GiantLeap helps teams break through to customers, break away from competitors, and capture markets.


Dynamic, Efficient, Market Driven

In six to eight weeks, we deliver a positioning strategy, messaging platform and sales enablement toolkit that unify sales and marketing, motivate buyers and accelerate market capture.

Focused Workshop

A highly structured, one-day offsite with your team to clarify the problem you solve, profile your target buyer, highlight reasons to act and document your differentiation.

Rapid Prototyping

Market ready messaging and positioning story creation, including all visual language, completed from workshop content and honed in weekly reviews.

Market Validation

Structured review of draft story and messages with market experts in face-to-face meetings to harden the concepts and tighten delivery.

Sales Enablement

Development of, and training on, a sales playbook that helps sales professionals target and qualify faster, and align sales conversations to the company’s positioning platform.

Executive Support

Weekly telephone consulting to answer new issues and competitor response and guide application of messaging into derivative works such as thought leadership, web copy, campaigns, PR, etc

Unlike doing it yourself – which is expensive, time consuming and doesn’t leverage outside perspective – the GiantLeap approach is efficient, market driven and led by experienced technology marketing leaders.


At the conclusion of your GiantLeap project, your team will be ready to use three market-validated documents that establish a strong foundation for sales growth.

Market Positioning Story

A high-impact presentation that clearly defines the problem you solve, your differentiated solution, and your unique position in the market for customers, partners and employees.

Messaging Guide

A long-form summary of your positioning strategy and story, messaging platform, and key copy blocks designed to help marketing professionals amplify your value proposition.

Sales Playbook

A practical, accessible guide for sales professionals to use as they convey your value proposition to their prospective customers.


Led and delivered by experienced technology marketing and sales professionals who understand that time is money.


Delivers a market-tested positioning story, messaging guide and sales playbook within ten weeks.


Prioritizes knowledge sharing, alignment, and consensus so your team is prepared and motivated.


Requires no more than two one-day team workshops.

3com-nontransOne of the early giants of networking, 3COM had seen its market advantage usurped by Cisco and other networking leaders. After a game-changer acquisition of a Chinese joint venture, H3C, 3COM retained us to re-vitalize its brand and bring the company back to life as a new “disruptor” in the networking business. By successfully positioning its “China-out” strategy, 3Com supplanted business as usual in the enterprise networking and security market outside the US.

Subsequent engagements with wholly owned Tipping Point security re-positioned this Gartner-recognized intrusion prevention category leader into the comprehensive inline security solution for the most demanding next generation data centers. As a result, the company was able to clearly articulate the distinct value and differentiation of the new 3COM and added $1B valuation to the company in 6 months. Within one year, HP successfully acquired the company for $2.7B

By eliminating distance and location as constraints for delivering applications, Riverbed created the category for wan acceleration. However, they too often were perceived as living in the market shadow of Cisco. In order reach its next level of revenue growth, the company aspired to transition from a niche vendor to a strategic networking supplier.

Our project successfully developed a compelling, business-level conversation for reaching the CIO, helped Riverbed move higher in sales cycles and strengthened their competitive positioning. As a result of this effort Riverbed proved the value of wan acceleration, grew market share in a down economy, and enjoyed a 3x market capitalization growth in the subsequent 2 years.

Chordiant Software became an ~$80 million public company after acquiring additional analytics assets to deliver operational CRM. Their clients serve “millions of customers” such as subscribers in the cell phone, banking and health insurance industries.

Our engagement created an umbrella positioning strategy that unified Chordiant’s predictive and adaptive applications to help global brands multiply customer lifetime value. Six months later Chordiant grew 46% in one quarter before accepting acquisition by Pega Systems for 31% share premium.

As the market for virtualization matured, we helped this category creator expand their selling efforts to other buyers and markets, solidify their leadership role in accounts and strengthen their competitive position against new entrants.

Retained by sales operations, our engagement developed “Fight Plan” sales enablement tools to help the field and channel organizations identify sales scenarios, engage multiple buyer/roles and combat competitive pressures in sales cycles. These 4 page playbooks bridged the divide between marketing and sales by turning the VMware positioning messages into buyer-centric sales conversations. Aligned with VMware sales processes, this initiative optimized the key messages and delivered them in situational, role-based, sales relevant package tailored to the needs of the VMware direct or indirect channel needs.

Within a year, our Fight Plans became among the most popular downloads from the 1000+ content documents on the VMware sales operations portal.

After acquiring companies in an effort to transition their overall offering, WebEx retained us to adapt their positioning to appeal to increase stickiness, sell to a broader market, enable a larger sales transaction, and to drive a higher valuation of the company.

By repositioning WebEx as a SaaS platform, the company was able to drive higher revenues, raise their valuation and deliver a broader solutions platform to the marketplace. WebEx was acquired within a year by Cisco for a 22% share premium.

After growing to a $50M SaaS business, Taleo’s leadership position was threatened by new competitors and shift in the buying climate.Taleo retained us to protect and grow its leadership position, evolve the positioning of the company and strengthen its competitiveness in sales cycles.

Mike Gregoire, CEO, explained in a subsequent podcast interview how our 4 projects helped his company quadruple revenues to $200M in 4 years while growing margins 42% in 2009. Taleo was purchased by Oracle for $1.9B, an 18% share premium.

After acquiring BrightMail, Symantec had achieved a leadership position for integrated message protection in the large enterprise. To achieve its business unit revenue and market share objectives, Symantec had to take advantage of a tremendous unsold opportunity in the VAR channel and SMB market. In this market, Symantec’s leadership position was being threatened by strong competitive threats and lost VAR mindshare.

Symantec retained us to conduct a positioning and operational assessment, followed by re-positioning and go-to- market strategy for the SMS product line.

Within a year after our services, Symantec doubled quarterly transactions and re-gained 2.5% market share against its competitors. Subsequent projects included positioning Vontu DLP for global channel sales, C-Level positioning for Information Management Group, and Partner Sales enablement for Symantec’s Global Alliance office.

After making a strategic decision to enter the automotive dealership market, SAP retained us to help galvanize a far-flung executive and product team and uniquely position and launch the global dealership management solution against well-established competitors.

As a result, SAP consistently delivered a high-impact positioning story, successfully launched the solution in key countries and realized its customer acquisition goals for this new product line.

Before completing development of Oslo, a new innovative SaaS application development platform, Microsoft retained us to examine their current positioning messages, develop a compelling, fresh positioning story and field sales playbook.

The engagement included an approach for progressively disclosing the Olso (now Azure) story over an 18 month period, in order to shape the market category and protect revenue from existing product lines.

Through this effort, Microsoft successfully conditioned the market for a series of subsequent launch events, enabled the field organization with positioning sales conversations and leveraged Oslo to ramp sales BizTalk.

Video Resources
Video Information

The Wharton Entrepreneurs Workshop, developed jointly by Wharton, San Francisco, and Wilson Sonsini Goodrich & Rosati, features Chris Roon.

Using real-world examples, Chris demonstrates the effective use of great positioning principles and go-to-market strategies by successful Silicon Valley companies.

Chris Roon - Partner

Chris spent the first 20 years of his operating career leading technology companies into share-taking battles in tough markets. Chris pioneered software product offerings, business models, and partnerships that helped create the enterprise resource planning, supply chain, and social CRM categories. As a go-to-market strategy consultant since 2005, Chris has helped general managers and entrepreneurs take ideas ahead of the curve into the mainstream.

Chris was VP of Product Strategy at where he contributed to the early creation of the Application Exchange. While VP of Strategy at PeopleSoft, Chris led the transformation of the company’s global services organization to $1B+ service chain. As CMO at Red Pepper Software, Chis created partner and positioning strategies that led to rapid growth and a successful exit. During nearly 5 years in product management at Oracle, Chris designed, developed and brought to market the manufacturing order management suite.

Chris received his Bachelor of Science in Geology from Occidental College, and his MBA from Dartmouth Tuck School.

Paul Reddy - Partner

Paul is an operating leader with 25 years of experience in sales, marketing and strategy.

Paul joined Chris to form GiantLeap after serving as the founding CEO of Zaniac, an after-school program developed to get K-8 students engaged in STEM subjects. He previously served as President of Datamark, the leading direct/digital advertising agency serving post-secondary education.

Before Datamark, Paul led the marketing, sales and client service teams at InsideTrack,  a pioneering provider of customer retention solutions in higher ed. He was a co-founder of software-as-a-service provider Spoke Software, led business/corporate development for PeoplePC, and was a Principal with management consultancy A.T. Kearney. Paul is also a founding partner in Newpark Capital, a mid-market private equity firm.

Paul graduated from Northwestern University with a Bachelor of Arts in Economics and Political Science, and earned his MBA from Stanford University’s Graduate School of Business.

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