Enablement

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Sales Enablement Guiding Principles

  • Hire sales enablement leaders who are expert and project and program management. But, do not have them run training sessions. Similarly, do not hire full-time trainers from the outside (or contract with outside sales trainers). Either:
    • Rotate people in-out of sales enablement. They teach the classes but also get attached to deals to support (newer) reps and (newer) managers. When you rotate them out, put them in bigger jobs. Ex: AE to enablement to first line management; first line manager to enablement to second line manager.
    • Rely on active reps and manager to train. Certify and support them by ‘training-the-trainer.’
  • Get top-level executive buy-in (CEO & CRO) for all enablement initiatives
  • Train & certify first line sales managers before training reps. This is an absolute non-negotiable.

Sales Playbook

I find it is best to think of a sales playbook not as a single asset but rather as a collection for resources that comprise the operating system of a sales team. In many ways, this website is itself a sales playbook.

Here are some of the more common elements to include in your sales playbook:

  • Sales Process & Tools
    • Territory management
    • Sales process stages with definitions, buyer/seller exit criteria, etc.
    • Campaigns
    • Prospecting cadences/sequences incl. messaging
    • Qualification / deal health framework (ex: MEDDPICC; Discovery guide)
    • Proposal / solution development
    • Objection handling guide
    • Common deal scenarios and obstacles
    • CPQ workflow
    • Handoff to customer success
    • Meeting/call methodology (pre, during, post)
    • Operating rhythm/cadence for pipeline & forecast management
    • Guide to using various sales tools (esp. CRM, CPQ; data services; sales engagement; sales enablement; etc.)
    • Call library (esp. sequence of calls from start to finish if a closed won deal)
  • Company
    • Culture, values, & expectations
    • Roles (definitions & expectations; career paths)
    • History
  • Product
    • Value proposition / ROI and unique differentiation / critical capabilities
    • Use cases & success stories
    • Features & functionality
    • Demoing
    • Competitive landscape / positioning / battlecards
    • Contracting and pricing policies
  • Sales Skills
    • Negotiating; objection handling approach; storytelling; listening / questioning; account planning; cross-selling / upselling; customer conflict resolution; etc.
    • Internal partnering (esp. Marketing; Product; Legal)
  • Industry & Market
    • ICP & persona definitions (case studies with why they bought and what they achieved; breakdown by size / geo / industry)
    • Business acumen
  • Other
    • KPIs (dashboards; benchmarks, etc.)
    • Access to content (pitch deck; case studies; proposal templates; mutual plans; account plans; etc.)
    • Sales management guides (esp. hiring, coaching, performance management)

Sales Training

For training to succeed, one must first determine priorities across the following:

  1. Process & Methodologies (incl. selling skills)
  2. Market/Customer Knowledge
  3. Product knowledge
  4. Tech stack/systems knowledge
  5. Soft skills (ex: time management; communication; leadership)

Next, align leadership starting with the CRO in larger companies and with the CEO in smaller ones. Work your way down with special emphasis on training/certifying first level managers. Only then, train & certify reps.

Measuring Return (ROI) on Sales Enablement

I’ve never seen a successful/sustained ability to measure return on enablement. To really do so, you’d have to A/B test. Even without A/B testing, perhaps you could measure ramp time but one would need to define that (ex: time to $x of bookings) since time to full quota assignment is arbitrary and tie to 100% quota attainment would mean many never ever ramp. Ongoing training is even harder if not impossible. My guidance is:

  • Set a ratio of revenue team:enablement (median ratio of revenue professionals – AE/AM, CSM, SDR, & Sales Eng. – to enablement professionals is 43:1)
  • Let the enablement people do their job; you’ll ‘know’ if they are effective or not

Should one still attempt to measure, here are a number of KPIs:

Sales Performance Metrics

  • Pipeline generation ($ or #)
  • Win Rate
  • ASP
  • Sales Cycle Time
  • NRR, GRR
  • Discount rates

Program & Content Engagement

  • Content/page views, view duration, & quality ratings [by sellers or among buyers]
  • External content shares per rep (#)
  • Quiz scores (applies assessments like pitch practice)
  • Module/course completions (# and/or participation rate) & certifications
  • Module/course CSAT
  • Revenue influenced (based on closed won deals where buyers engaged with content that was shared)

Productivity

  • Ramp time – I recommend time to X% of quota (consider 20% since 100% tough) or time to $y booked (see here for more)
  • Time to certification
  • Quota Attainment
  • ARR/AE (cohort as <1 year, 1-2 years over 2 years)
  • Rep Attrition & employee engagement (eNPS)
  • Funnel conversion rates (ex: MQL to SQO)
  • Sales stage-to-stage conversion rates and cycle time (beware: increasing early stage conversion rates can be bad for the business if late stage rates drop; hence, one must track overall win rate as well)

Enablement Team Measures

  • Project / MBO completion

Other Measures (often tied to common growth initiatives)

  • Forecast accuracy
  • Bookings mix by product (esp. for new product launches)
  • Coaching interactions
    • # conversational intelligence call reviews completed
    • Manager participation rate
  • Contacts per opportunity (for multi-threading)
  • Loss rate due to various reasons (esp. loss to specific competitors)
  • Message adoption (measurable via conversation intelligence)
  • Sales process adherence (hard to measure)
  • Tool adoption
  • Sales expense / (new + expansion bookings)
  • Manager assessment of rep capability

Internal Sales Communications Strategy

Once a company exceeds about 20 sellers (and certainly once a company is multi-product), it becomes critical to protect sellers’ time and attention by controlling communication.

  1. Funnel any/all communications to sales through a central function (sales enablement and/or sales comms).  Product, marketing, etc, should no longer be able send directly to sales distribution list.
  2. Combine general sales communications into a periodic newsletter. More generally, intentionally leverage the various channels at your disposal: sales managers; team meetings; etc.
  3. Communications to sales should be prioritized as follows:
    1. High: conduct training & certification
    2. Med: – include in regular newsletter to sales
    3. Low: – do not send to sales
  4. When messaging sales (high & med priority comms), link features to value, talk tracks, use cases, case studies, etc.

Sales Enablement Budget

Source; Gartner 2022

Enablement Ratios

The following is the ratio of revenue professionals (AE/AM, CSM, SDR, & Sales Eng.) to enablement professionals based on the Cloud 100 as of Jan 16, 2023.

Total
Employees		Median
Ratio		Average
Ratio
286 to 60039:141:1
601 to 90035:147:1
901 to 1,15050:163:1
1,151 plus44:160:1
Overall43:155:1

The following queries were used to determine counts using LinkedIn Sales Navigator:

  • AE/AM: (“account executive” OR “account manager” OR “account representative” OR “sales executive” OR “sales manager” OR “sales representative” OR “sales associate” OR “territory manager” OR “strategic account” OR “strategic accounts” OR “partner sales” OR “channel sales” OR “major account” OR “major accounts” OR “account director” OR “sales director” OR “business development” OR “enterprise AE” OR “mid market AE” OR “strategic AE” OR “SMB AE” OR “senior AE” OR “senior AE” OR “AE Team Lead”) AND (NOT(“business development representative” OR enablement OR operations OR technical OR “sales development”))
  • SDR: SDR OR “sales development” OR BDR OR “business development representative” OR “inbound sales” OR “lead development” OR ldr OR “lead response” OR “market response” OR “account development” OR adr
  • CSM: (“customer success” OR csm OR “client partner” OR “client engagement” OR “customer engagement” OR “client strategy” OR “technical account manager”) AND (NOT(operations OR enablement))
  • Enablement: (sales OR revenue OR growth OR gtm OR success OR bdr OR sdr) AND (enablement OR training OR effectiveness OR facilitator OR readiness) AND (NOT(channel OR partner))
  • Sales Eng.: “sales engineer” OR “sales engineering” OR “solution engineer” OR “solution engineering” OR “solutions engineer” OR “solutions engineering” OR “sales consultant” OR “presales” OR “solutions consultant”

Sales Enablement Compensation

According to Glassdoor (as of March 2023), the most likely range for Sales Enablement manager OTE is $110K to $180K with a median of $140K and 75/25 variable split (with a range of 70/30 to 80/20).

Since return on sales enablement is notoriously difficult to measure, bonuses may depend on:

  • Company ARR attainment
  • MBOs tied to enablement initiatives (may be qualitative or quantitative)

Sales Enablement Tools

(*) = recommended

Sales Trainers, Consultants, and Communities

(in alphabetical order; (*) = recommended)

Footnotes

1 Showpad is an Insight Partners portfolio company.  The editor of this page is employed by Insight Partners.

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