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The 50 Question RevOps Maturity Assessment

Asking the Right RevOps Questions to Scale Your Company

Imagine having a brand new Ferrari in your garage with every available upgrade.  Now imagine not knowing how to drive.  Suddenly, a machine capable of transporting you anywhere you desire at a high rate of speed is rendered useless by a lack of knowledge.  In a similar way, many organizations have access to vast amounts of revenue data capable of maximizing their potential for growth, but that data’s value is not realized due to an absence of know-how.  Data must be collected, synthesized, and disseminated in the correct way. 

That’s what RevOps done well is all about.  When an organization does this, they can know what happened (hindsight), know what is happening (insight) and know what will happen (foresight).  The importance of RevOps cannot be understated.  In conjunction with this, the importance of revenue maturity must not be ignored.

Reaching RevOps Maturity

If your child kicks dirt into the face of another child, that’s a sign of a maturity issue.  If your sales and marketing teams are “kicking dirt” in each other’s faces through misaligned goals and confusion regarding product pricing, that’s also a sign of a maturity issue.  A revenue maturity issue.  Many companies fail to reach revenue maturity, and, subsequently, fail to obtain long-term, scalable growth.  What questions should be asked or steps taken to successfully reach revenue maturity?  Fortunately, Jeremy Donovan of Insight Partners has developed an assessment to guide your company to growth.  The assessment is comprised of 50 questions and the following 9 blocks: 

  • GTM Strategy

  • Sales Process 

  • Customer Success and Support Process

  • Sales Compensation and Quotas

  • Pipeline and Forecast

  • Sales Leadership, Team Effectiveness, and Cross-Functional Collaboration

  • Technology and Data Governance

  • Hiring and Talent Management

  • Order to Cash  

The Why and the How of this RevOps Assessment

This assessment is a template to help guide you in asking the right questions.  The blocks cited above encompass all aspects of your organization’s ability to accurately assess your level of revenue maturity and identify where areas of opportunity exist.  The ultimate goal is, of course, the alignment of sales, marketing, systems, and processes within your organization.  Although the questions below are valuable in and of themselves, their benefits can be expanded by DMing Jeremy for a link to the survey.  By doing this, you will immediately be given a benchmark scorecard to see how you compare to others.  Many have already completed the survey, so a solid set of this data is available.  This data will then enable you to create a hierarchy of needs and improvements within your organization and determine the financial feasibility of each.

Now, let’s get started! 

RevOps Maturity Assessment Questions

 GTM Strategy 
  • Our sellers can pitch our solution in a consistent manner that differentiates our value proposition from the competition.  
  • We use clear account segmentation to allocate marketing and sales resources.  
  • Our sellers have assigned accounts in equitable territories based on size, industry, geography, and/or other relevant segmentation criteria.  
  • We have identified the types of accounts we should not sell to, I.e. companies that are costly to serve and/or difficult to retain.  
  • We know how to access the right buyer personas at organizations fitting our ideal company profile and have documented personas and ICPs.  
  • We have targets for net new revenue contribution by source (ex: product-led, marketing-led, SDR-led, AE-led, partner-led, etc.)  
  • Our revenue is neither concentrated with a small number of customers nor in a single vertical market.  
  • We actively manage partner channel conflict using rules of engagement and systems (ex: deal registration).  

Sales Process 

  • Sellers in each segment follow a documented, multi-stage sales process with adherence to exit criteria.  
  • Our sales process has enough steps that we can adequately track deal progression and make decisions based on that information  
  • Our salespeople (AEs, SDRs/BDR, etc.) follow a qualification methodology to ensure only high-quality leads convert to opportunities.  
  • Sales and marketing are aligned on top-of-funnel strategy for each segment.  
  • Marketing and Sales work together to develop and execute pipeline generation strategies.  
  • We follow a data-driven approach to optimizing our sales process that considers activity, effectiveness, and results.  
  • Our inbound leads are rapidly scored and routed for qualification by SDRs or AEs.  
  • Sellers are mapping stakeholders and influencers in the sale.  
  • We have robust content/collateral available for coordinated campaigns as well as ad-hoc use.  
  • We create and present demos based on specific use cases/pain points outlined with the customer.  

Customer Success & Support Process 

  • We have a differentiated service and success approach based on customer segment (ex: high touch, low touch, tech touch).  
  • We proactively engage clients to drive value-realization, satisfaction, adoption (usage), and engagement.  
  • We measure customer health and respond rapidly to address issues.  
  • Our renewal process all but ensures on-time renewal.  

Sales Compensation & Quotas 

  • Our sales compensation plan is directly aligned with our key corporate objectives.  
  • Over 60% of our salespeople meet or exceed quota in every period.  
  • Our sales compensation plan is simple for reps to understand and easy to administer. (For example, the plan uses no more than 3 key performance measures weighted at least 20% each.)  
  • Quota is at industry benchmark 5x on-target earnings or is adjusted in a way that makes sense for the business.  
  • We have consistent compensation ranges for each role in the sales organization that are competitive by role and geography.  
  • Sales reps are at 50/50 base to bonus or that ratio is adjusted in a way that makes sense for the business.  
  • Our sales compensation plan offers generous (2x or higher) accelerators to sales reps should they exceed quota.   

Pipeline & Forecast 

  • We have a large enough pipeline to achieve bookings goals in each period given sales cycles and win rates.  
  • Sales cycles are predictable by segment and consistent with industry standards.  
  • We have an operating rhythm in place to help advance key deals this period and next period that engages all levels of sales leadership.  
  • We monitor and report on pipeline created per seller on a frequent (ex: weekly) basis.  
  • We have a deal desk to support sellers on complex opportunities.  
  • We work to keep net retention above 115% and have a strong focus on cross-sell and upsell.  
  • We work to keep gross retention above 85% and take action to discourage downgrades and prevent churn.  

Sales Leadership, Team Effectiveness, & Cross-Functional Collaboration 

  • Responsibilities for each of our pre- and post-sale roles are well-defined. (ex: SDRs, AEs/AMs, Sales/Value Engineers, CSMs, Renewal Specialists, Implementation/customer onboarding, Technical Account Managers, etc.).  
  • Our attrition rate is well below industry standards.
  • Our sales & product organizations are well-aligned. 
  • Sales Leaders monitor rep performance and pipeline generation and provide coaching and support to ensure ongoing success.  

Technology and Data Governance 

  • CRM data (activities, contacts, accounts, opportunities, etc.) is consistently captured and cleaned.  
  • We have a marketing automation platform/tool in place that rapidly matches qualified leads with sales professionals.  
  • We have reports, dashboards, and business intelligence tools that provide an up-to-date view on how our business is performing relative to targets.  
  • We have a customer success platform/tool (or equivalent) to monitor/manage customer health and product adoption.  
  • We have one or more dedicated Salesforce/HubSpot Administrator(s).
  • Our CRM has roles and permission sets enabled (I.e. individuals have read/write privileges restricted only to what they ‘need to know’).  
  • Customer data such as billing, usage, product configuration, etc. are easily accessible to those who need access.  

Hiring & Talent Management 

  • We leverage ideal hiring profiles and a repeatable hiring process that consistently selects great sales and sales support talent.  
  • Recruiting is a proactive, scalable process that ensures that roles are quickly filled.  
  • Our hiring plan for sellers and sales support roles ensures we have ramped capacity to meet our financial goals.  
  • We have in-house recruiting resources to aid in filling sales roles.  
  • We have a programmatic approach to onboarding new talent and a documented enablement plan to skill them up quickly.  
  • Enablement is managed by a formal team within the sales organization.  
  • Management is actively engaged in the enablement process and reinforces the training through 1:1 coaching, team training, and role-playing.  
  • We have documented career paths for all roles that are motivating and achievable.  

Order to Cash 

  • We have strong controls in place to minimize errors in the order entry and billing process.  
  • There is a clearly documented and automated process extract from the CRM and load it into our billing/finance tools.  
  • Financial systems and sales systems either use the same customer identifier or have a means of mapping customers from one system into another system.  
  • There is a workflow in place for automatic renewals and price increases.

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