Founder Sales Diagnostics
Diagnose the sales challenge. Design the right intervention.
Before investing in sales training, hiring, incentives or new systems, founders need a clear understanding of what is affecting sales performance.
A conversion problem may originate in unclear target customer profiling, lead qualification or an ineffective sales process. Low sales team productivity may reflect unclear responsibilities, fragmented information or a compensation structure that rewards the wrong behaviours. Each requires a different response.
SalesWomentoring’s Founder Sales Diagnostics examines these connections in the context of the business’s growth goals. Led by Chitra Singh, the diagnostic identifies the underlying barriers to performance and establishes the basis for a customised sales intervention.
The objective is to direct investment and effort towards changes that can make a meaningful difference to business growth.
Built around the business and its growth goals
Every business brings a different combination of customers, sales channels, team capabilities and operational constraints.
The diagnostic begins with the founder’s business objectives and the sales decisions that need to be made. The scope is then tailored to the questions that matter most.
These may include:
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What needs to change for sales to grow without increasing dependence on the founder?
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Why are sales activity and lead volumes failing to translate into sufficient conversions?
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Does the sales structure support the next stage of growth?
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Are compensation and performance measures encouraging the right outcomes?
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What is preventing the sales team from using its time effectively?
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Does the founder have the information needed to review sales growth and make sound sales decisions?
The review examines how these issues interact, so the proposed intervention addresses the underlying problem.
What the diagnostic examines
The areas reviewed depend on the business context and the agreed scope.
Sales strategy and customer focus
Assess the alignment between growth goals, target customers, value proposition and routes to market. Establish whether sales effort is directed towards the customers and opportunities the business is best positioned to serve.
Sales process and conversion
Examine how opportunities move from enquiry through qualification, customer conversations, proposals, negotiation and closure. Identify where progress slows, opportunities are lost or the founder’s intervention becomes necessary.
Sales structure and accountability
Review roles, responsibilities, decision-making authority and leadership requirements. Assess whether the structure enables effective execution and provides clear ownership of sales outcomes.
Sales team productivity and capability
Examine how selling time is allocated and the practical barriers affecting performance. Identify whether improvement requires stronger skills, clearer processes, better information or changes in management practices
Compensation and performance measures
Review how KRAs, KPIs and incentives influence sales behaviour. Assess their alignment with the business’s commercial objectives, quality expectations and growth plans.
Reporting, systems and sales governance
Examine whether reporting and review practices provide a reliable view of pipeline movement, conversion and performance. Identify gaps that prevent timely decisions, consistent follow-through or effective coordination.
From diagnosis to a customised intervention
1. From diagnosis to a customised intervention
The founder and Chitra Singh establish the commercial challenge, the outcomes required and the decisions the diagnostic needs to inform. This provides a clear purpose for the review.
2. Examine the evidence and operating context
A structured questionnaire, relevant sales information and focused discussions help establish how sales works in practice. The review considers the business’s existing capabilities, resources and constraints.
3. Identify the causes and design the response
Findings are translated into recommendations that connect each identified gap to an appropriate intervention. Depending on the diagnosis, this may involve sales strategy, process redesign, team structure, compensation, capability development or ongoing advisory support.
4. Establish how progress will be assessed
The proposed changes are linked to relevant milestones and measures of success. Depending on the engagement, these may include conversion, sales cycle length, sales team productivity, pipeline visibility, CAC/ CLV ratio or clearer ownership and execution.
The scope, outputs and measures are agreed for each engagement.
A clear connection between the work and its business impact
The diagnostic provides a reasoned basis for deciding where to intervene and what the business should expect the intervention to improve.
For example, if opportunities are being lost because leads are poorly qualified, the response should address lead qualification criteria and sales discipline. If the team lacks negotiation capability, customised training and practice may be appropriate. If incentives encourage behaviour that undermines commercial goals, the compensation structure needs attention.
This connection between diagnosis, intervention and measurement helps the founder make informed investment decisions and assess whether the changes are producing the intended effect.
Taking the findings into execution
For founders to work through strategic sales decisions in depth, The One Day Founder Sales Accelerator, an intensive one-day, 1:1 advisory session focussed on sales strategy, structure, compensation and governance follows the diagnostic. The engagement produces a Founder Sales Blueprint to guide execution.
The 90-Day Founder Sales Advisory supports the implementation of strategic sales decisions through regular guidance and course correction. It can follow the Accelerator or be undertaken as a standalone engagement.
The appropriate form of support is determined by the business’s needs and the scope of change required.
Led by Chitra Singh
Chitra Singh is an award-winning Sales Consultant, Founder Advisor, Corporate Sales Trainer and Sales Mentor with 27+ years of experience, including leadership roles with ICICI and Kotak. As Founder of SalesWomentoring, she helps founders and organisations strengthen sales strategy, capability and execution.
She has mentored 2,000+ founders and professionals, with mentoring engagements including Goldman Sachs 10,000 Women at IIM Lucknow, NASSCOM, WEP-NITI Aayog and the Wadhwani Foundation. Her recognition includes the HerRising Award (2023), Sales Collective’s Women in Sales to Follow (2024) and features in YourStory, among others.
