Guiding Questions

What assumptions made during earlier phases (Product Strategy and MVS) about buyer and user behaviors have been validated or debunked?

What are the team-level responsibilities during each stage of the customer acquisition process? For example, how does Sales interact with Customer Success to ensure effective onboarding?

What are the measurable indicators that tell you if a customer is using the product efficiently when onboarding?

What attributes are common to customers who struggled to realize value during the MVS phase (e.g. low technical acumen, thus slow to integrate and onboard)?

What product utilization patterns were common to customers who succeeded or failed during the MVS phase?

What company skill gaps do you need to address (train, outsource, hire) prior to launch?

What technology and educational material can you introduce to reduce friction for customers?

What is the customer acquisition (revenue) target for your first year in-market?

What is your year-one margin expectations?

How many new customers do you need to onboard (per each tier) on an annual, quarterly, monthly basis, to meet your revenue target?

How much will it cost you to onboard these customers? What is the budget for CAC, inclusive of comprehensive sales and marketing costs?

Do you have the skills and resources to acquire new customers and stand them up, at a pace in-line with your targets?

How long will it take to recover CAC for a new customer?

How much flexibility do you have with your discount strategy?

For transformation scenarios, how and when will you deprecate the legacy solution? How will you structure revenue quotas for the legacy model as its sunsets?

For transformation scenarios - do your investors and executive leaders understand the economic ramifications of transforming to a SaaS model, the required investment, and the transition from up-front payments to recurring revenue streams?

What is an acceptable annual churn (revenue)?

How much churn may come from down-sizing customers to more-appropriate offer tiers?

How much churn may come from customers declining to renew, or exiting early?

How complex are expansion and renewal negotiations?

What are your CEC and CRC budgets?

How long can you expect to retain a customer?

What is your expected CLTV?

What is your target CLTV to Total CAC (CAC / CEC / CRC) Ratio?

For transformation scenarios, are you migrating customers to SaaS from an on-premises legacy solution? If so, when? What are the economic impacts?

Do you align dedicated sales representatives to specific offer tiers/geographies/verticals? Will this differ from your legacy operation?

How many sales representatives can you dedicate to the SaaS model, given CAC budgets?

Can you leverage a remote inside sales team to generate qualified leads and/or deliver solution demos, as part of the pre-sales process?

What information do you need to discover during the pre-sales process to properly qualify prospects likely-to-succeed, and thus reduce downstream churn?

Will the customer acquisition quota include customers migrated from legacy solutions?

Who will own renewals and expansion revenue quotas?

How complex are your negotiations? Do they require a high-touch consultative approach? Can you simplify the process?

Are your sales teams enabled, and able to articulate the unit economics and competitive value proposition which underpin your pricing and services?

What is your strategy to land a customer, and then, expand the relationship?

Can you define data-driven up-sell opportunities?

What role will channel partners play in your sales model?

Can you enable channel partners to drive the adoption of your services?

What compensation incentives can you offer our Sales representatives to reward product adoption and retention?

How do you measure the quality of a new lead? How can you tell if a lead is likely to succeed in using your platform?

How will Marketing team interact with product teams, to create and execute product marketing initiatives?

What are the demand generation → lead generation → customer conversion funnel ratios you need to achieve, in order to support customer acquisition objectives for year-one?

How will marketing and sales teams divide responsibilities associated with funnel management?

What technology can you introduce to make lead qualification and lead scoring processes efficient?

Can you publish content (videos, user manuals, FAQs) to educate customers and reduce friction during the sales process?

How will you market to customers ahead of a new feature release, to support expand-selling motions?

What focus groups should you use to analyze the effectiveness and profitability of your marketing campaigns? Offer-level? Vintage/time-based? Channel-based?

What is the primary aim for the CS team? Expansion? Product adoption? Renewal?

Who owns the customer relationship with the deciding party, during renewal?

Will CS carry a revenue quota for expansion or retention?

Can you monetize the CS team by selling it as a premium service?

What role does the CS team play in coordinating cross-functional activities with other teams?

Will CS also provide Customer Support?

Will you align CS representatives with customers based on tier, industry or vertical expertise?

How many customers can each CS representative manage effectively on an annual basis?

Where will you find CS representatives? What skills should they possess?

How many CS representatives can you fund, and (as appropriate) how much up-sell and cross-sell revenue can you drive, given your CEC and CRC budgets?

What is important for your target audience? What type of information do they need or expect from you?

What is your communication goal (e.g. number of users/accounts reach, product/feature adoption, revenue, etc.)?

What’s the best way to reach out to your target audience? How can you leverage multiple channels to create an immersive experience?

How are your customers impacted? Do some of your customers need additional support to communicate the product updates and train their employees?

What should be the timing of this communication? How much time do your customers need to adopt new features/releases?

Do you have any commitments to let customers know certain changes in advance?

How can you a/b test your message?

Do you have a mechanism for your customers to provide feedback about product communications and suggest new features to be developed?

What are the most important metrics to measure reach, engagement, and adoption? How can you optimize your plan for next iteration?