(Note: Sramana, our guest for the Startup Success Podcast Show #52, was kind enough to let me reprint here the appendix of her new book, Positioning: How To Test, Validate, And Bring Your Idea To Market. These are the kinds of “killer questions” you need to think on, research and define your unique answers for.)
Excerpt from Positioning: How To Test, Validate, and Bring Your Idea To Market
by Sramana Mitra

For Enterprise- and SME-Facing Businesses: This set of questions will help you through the process of testing and validating your idea while building an effective Go-to-Market strategy for a B-to-B venture.
Product or Service Value Proposition:
• What pain does your product/service address?
• What is the profile of your ideal target customer (company)?
• What is the profile of your ideal target user (within the target company)?
• What is your technology?
• What is the application of this technology?
• What are some compelling use cases?
• What is your differentiated, must-have value proposition to this customer?
• Which market? Which segment? Why?
• How big is the market? Is it big enough? How do you expand, if not? Should you expand, or should you focus within a niche?
• What is the usage model of the product?
• How does the user currently solve the problem in question?
• Who is the buyer?
• How strong is the pain? Does the buyer care to solve the user’s pain?
• How do you prove your value? Pilot? Free trial for a month? Three months?
• How long does it take to prove value?
Competitive Positioning & Pricing:
• Who is the competition, and how do you differentiate from them?
• What are the various classes of products in immediate and related categories?
• What, of those, compete directly with you?
• Which ones are likely to move into your space?
• How do your product features compare with the competition’s? Can you compete on the basis of functionality?
• How does your product pricing compare with the competition’s? Can you compete on the basis of price?
• How do customers and prospects view your offering, vis-à-vis competition? Do they see you as 1/10 the functionality? 1/5 the functionality? 300% the functionality?
• What value does the customer see?
• What are customers willing to pay for your solution? 1/10 the key competitor’s price? Same price? 200% the price?
• What price can you charge based on perceived value?
• What is the ROI for the customer? How long will it take to realize the ROI?
• Can you offer both better performance and lower price?
• Whom do you need to partner with to offer a full solution?
• How do you position win-win deals for partners?
• Can you turn some of the competition to partners/channel/OEM relationships, so not to go head-to-head?
Sales Cycle & Messaging:
• What are the top target segments (verticals, size, geography)?
• What is a typical repeatable sales cycle for each segment?
• Who is the relevant VITO (Very Important Top Officer)/economic buyer (EB)?
• What job title does that correspond to within the target company/segment?
• Who is the technical decision maker (TDM)? What job title?
• Who is the user? What job title?
• Who is a likely champion for your solution? What job title?
• Who can coach you inside an account? How do you gather information required to qualify the lead? Extract the pain? Position the solution?
• What is your value proposition to the VITO/EB? TDM? User? Champion? Coach?
• How do you communicate that value in 20 words or less?
• What pain extraction questions correspond to that value? In other words, if a sales rep gets a relevant stakeholder on the phone, what should she ask? Or, what should she ask in a succinct email, to gain permission for further engagement?
Lead Generation & Qualification:
• What are the top target segments (verticals, size, geography)?
• What is the best way to generate a list of the target accounts within the segments?
• What job titles are we after within those accounts?
• What is the organizational map within the account that maps to the sales cycle?
• What are the names of the stakeholders who correspond with the economic buyer, the technical decision maker, etc.?
• What is the pain extraction question/value proposition message if someone with the right job title gets on the phone?
• What are the criteria for a qualified lead?
• What lead generation programs do you plan to pursue? Google PPC advertising? E-mail campaigns? Tradeshows? Other forms of online advertising?
• How do you plan to qualify the leads? Telemarketing? Outsourced? In-house?
Sales & Business Development:
• What is the appropriate channel strategy (direct, OEM, resellers, system integrators, telesales)?
• Are there channel conflicts? How do you resolve?
• What is your territory plan and prioritization, based on market segment targets?
• What paid proof-of-concept/pilot engagement/evaluation framework will get you to a deal within a short time?
• What are the appropriate sales cycle steps, next steps, and duration breakdown?
• What is the likelihood of a deal by sales cycle steps? How do you forecast?
• What are the must-have key target accounts? Why? What do you need to accomplish in those engagements to be able to achieve high leverage for reference selling, proof-points, and metrics?
• Do you have reference accounts? What is the best strategy to leverage the reference accounts and proof points?
• How do you build new reference accounts? Who is your target? Why? How do you penetrate, sell, and demonstrate ROI?
• Are there must-have channel relationships? What do you need to do to appropriately establish and manage them?
• What kind of channel discount do you need to provide to enlist the channel to perform on your behalf?
• Can you get OEM deals that may help you accelerate adoption?
• What is the product roadmap for the company?
• What is the unifying theme that positions the company and leverages its strengths (technology, product, channel, current customers, references, etc.)?
• Is there a platform strategy? A point-product strategy? A solution strategy? What holds all these pieces together? How do you position to make it into an integrated big story?
• What products/pieces need to be repositioned/repackaged to align with the corporate strategy?
• What is the full story? Is it a powerful, differentiated story that can go beyond a point-product/one-trick pony, to become a category leader?
• What is the category? Do you define a new category, or position within an existing one?
• What technology/product/channel/media elements need to be introduced/influenced to make it into a larger story?
• What broad scale industry trends can you impact based on your offering, and how do you position to align with such trends?
• What is your funding strategy? How do you position, package, and sell?
• What is your exit strategy? How do you position, package, and sell?
Execution Roadmap:
• What is your next major milestone? Product launch, funding round, exit?
• What derivative milestones/related projects do you need to accomplish to be able to stay on track and execute on the strategy?
• What is the project-resource-timeline map tracking to the next milestone?
• What is the messaging matrix?
• What is the collateral map, based on the sales process/sales cycle steps?
• What are the reference account milestones?
• What is the PR strategy?
• Do you have the resources to staff all the projects that lead up to the milestones?
• Who will manage lead sourcing/lead generation/lead qualification?
• Who will manage the PR process, pitches, follow-ups, etc.?
• Who will write the collateral? (Web site, sales pitches, data sheets)
• Who will design and produce the Web site?
• Who will manage events/tradeshows?
• What are the key additional hires/timeframe?
• Does everything align with your operating plan/budget? What tradeoffs do you need to make? What are the prioritization algorithms?
Sramana Mitra is a Silicon Valley entrepreneur who has founded three companies and provided strategy consulting to over 80 organizations, large and small. She writes a business blog, Sramana Mitra On Strategy, and is a columnist for Forbes. She is also the author of the Entrepreneur Journeys book series: Entrepreneur Journeys (Volume One), Bootstrapping: Weapon of Mass Reconstruction (Volume Two), and Positioning: How To Test, Validate, And Bring Your Idea To Market (Volume Three), all available from Amazon.com in paperback and Kindle, and from Smashwords.com in all e-book formats. Mitra has a Master’s degree in electrical engineering and computer science from the Massachusetts Institute of Technology.

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