Table of Contents

How to Shorten Sales Cycles & Increase Win Rates

Prospecting & Demand Generation
- Target the right the right ICP/persona to begin with
- Invest to drive inbound demand (demo requests or PLG sign ups)
- Invest in your brand (review sites; analyst firms; influencers; SEO, SEM, & social; etc.)
Opportunity Management
- Be clear about pricing early on; ensure pricing is competitive/attractive; if applicable, offer no-commitment, usage-based pricing; offer friendly payment terms
- Inspect deal health regularly (weekly) maintaining strict adherence to your sales process and applying your chosen qualification methodology
- Hypothesize then quantify the cost of continued inaction across each team involved in the buying decision
- Don’t waste time on activity that does not drive deals forward (ex: excessive 1:1 demos for end users)
- Get into legal early (ex: NDA)
- Simplify the contracting/legal process with fair, friendly terms; if possible, make terms non-negotiable
- Multi-thread
- Stay in frequent contact with your champion(s)
- Gain exceptional clarity on the who/how of the customer’s purchasing process. To do this, ask your champion to walk you through a prior purchase they make at their current company
- Assign the prospect homework specific to your value to maintain urgency.
- Hold firm on deadlines and set clear expectations about what you as a seller need in order to help them progress in their decision
- Provide access to self-service demos for new & existing stakeholders
- Help set prospects’ evaluation criteria; furthermore, help them rank as must have vs. nice to have
- Identify friction early and often; ask your champion directly about deal blockers be they human, technical, deal-related, etc.
- Don’t just send proposals, deliver proposal walkthroughs
- Create strong links to the prospect’s critical strategic initiatives
- Establish and maintain a mutual success plans such that every meeting ends with a clear next step that advances the sale
- Leverage executive alignment early and often
- Start with value-selling and shift to reducing post-sale risk (ex: share the distribution of implementation times); ensure one, easily attainable goal achieves the target ROI so that the rest is gravy
- Align with each team member during every interaction and follow up to remind them of that cost vs. your value
- Run tight PoCs/PoVs with agreed upon success criteria and broad stakeholder alignment. PoCs increase urgency by making opportunity costs tangible.
- Be prepared with references (for larger, late-stage deals); for smaller deals, provide overwhelming social proof via testimonials and case studies of similar brands
- Arm your champion with materials to help them sell internally (esp. to their CFO)
- Be direct with stakeholders. Hold them accountable to deadlines. Build enough trust to get clear answers when you ask, “Are we winning?”
Customer Success
- Deliver exceptional value, experience, & service to your existing customers

Best Practices for Running Proofs of Concept / Proofs of Value (PoC/PoV)

PoC/PoV Scope

Narrow the scope to a specific, high-priority use case
- Do not attempt to test every feature/scenario
- Be transparent about pilot limitations
Mutually define the measurable success criteria
- Agree on KPIs and ROI calculations
- Ensure processes & systems are in place to measure and share KPIs
- Get verbal (and contractual if possible) commitment that if/when the success criteria are met then the prospect will advance to the next step in the sales process (ideally signing the full contract)
Establish a realistic timeline with plenty of buffer to all but ensure success
- Keep it as short & simple as possible to achieve the success criteria
- Pre-schedule all external meetings including the kick-off, check-ins, and the final PoC/PoV review.
  - Kick-off
    - Insist the the final decision maker(s) and economic buyers are in attendance; hence, the kick-off must be business focused and not overly technical. Consider separating the business kickoff and the technical/user kickoff
  - Check-Ins: Gather feedback; answer questions & address concerns; share progress; adjust the plan & align on next steps
    - Check-in meetings will typically be held with your champion and user buyer(s)
    - Pre-set expectations on how you will update the economic buyer / decision maker(s). This will mostly likely be via email and is more powerful coming from your champion (with you cc’d); that being said, you should certainly draft on their behalf to control the message and to make it easy/effortless
  - Final PoC/PoV review:
    - Insist the the final decision maker(s) and economic buyers are in attendance; hence, this review must be business focused and not overly technical
    - Craft & deliver a post-PoC/PoV report that quantifies the value, addresses any open concerns, and serves as a clear business case for adoption of your full solution
- Pre-schedule key internal meetings; for example, prep calls in advance of each external meeting

PoC/PoV People

Identify & engage the decision makers, including the ultimate economic buyer (i.e. the person who actually signs the contract), the user buyers/influencers, and the technical buyers (ex: legal, security, procurement, etc.)
- Gather feedback from users throughout the PoC/PoV
Support the PoC/PoV with your dream team
- PoCs/PoVs are often run by sales support professionals rather than AEs/AMs. This includes: sales engineers; solution consultants; product specialists; value engineers; customer success managers; technical account managers/consultants; etc.
- Ensure strong executive sponsorship & alignment
- Engage external (channel) partners when relevant for influence and support; clearly define their roles, service level expectations, etc.

PoC/PoV Additional Tips

Unless achieving your LTV/CAC goals demands otherwise, do not let the prospect alone to run a self-guided PoC/PoV (which would really be a PLG motion rather than PoC/PoV motion)
- PoCs/PoVs are expensive from a customer acquisition cost (CAC) perspective so should only be done with well-qualified prospect in the middle-to-lage stages of the sales process. Consider having a rigorous/formal process for granting PoCs/PoVs.
Provide access to support documentation and fast-track support
Provide both on-demand and live demos & training
There is no right answer to whether to negotiate pricing & terms prior to the PoC/PoV.
- Pro case: Pre-negotiating allows you to transition from PoC/PoV to full contract seamlessly
- Con case: As a vendor, you will have a stronger negotiating position once the prospect has experienced the ROI of your solution
Run paid PoCs/PoVs
- This is of course easier when you have a strongly differentiated solution / limited competition
- Optionally, allow the cost of the PoC/PoV to be applied as a credit to your full solution
- Price the PoC/PoV at or above (but not below) the rate for your full solution
Throughout the PoC/PoV establish yourself as a true strategic partner not just a vendor by adding value/guidance beyond your solution

Negotiation & Discounting

Establish standards and limits on discounts reps can extend. Ideally, these should be ‘give-to-get’ only:

Volume based
Cash up-front (aka pre-payment)
Multi-year
Marketing clearance (case study; logo usage)
Referrals

Though I lack hard data on this, the conventional wisdom for discounting is as follows:

AE: up to 10%
1st line manager: up to 20%
2nd line leader: up to 30%
3rd line leader to CRO: up to 40%
CEO/CFO: > 40%

Driving Multi-Year Deals

Context for when you should maximize multi-year %
- High(ish) churn, esp. due to competitive pressure
- You have low NRR
  - You expect your pricing & packaging to remain stable.
  - You have sold ‘wall-to-wall’ such that upsell is limited. Multi-year deals can also somewhat inhibit cross-sell since the customer may feel, even if irrationally, that they have already purchased your complete solution.
- Complex implementation (esp. if not covered by additional professional services fees)
- Your margin is high or you otherwise expect stable/decreasing variable costs. Otherwise, you’ve locked yourself in to fixed income and escalating expenses.
- You have a strong brand and/or compelling differentiation such that reps encounter less-friction when positioning multi-year deals.
Pricing, Discounting, & Terms/Conditions
- Customers expect discounts and price lock-in.
- Stive to include annual price increases of CPI + x%. With fixed prices, the customer will likely be shocked at the end of the multi-year term by your new list prices. You can also get around this by pre-negotiating the price increase on the renewal at the end of the term; even if this is just an option extended to the customer, it serves as an expectation-setting anchor.
- It is very rare to get the entire payment up-front (~2%). If you expect to be acquired in the near(ish) future, you may not want full multi-year deal cash up-front since this constitutes cashless revenue obligations which are highly unattrative.
- Include an expansion rate table should the customer which to add additional seats or services during the contract term.
- Consider increasing discounts for longer term deals.
Sales:
- If multi-year deals are advantageous to your company, standardize that all deals must be multi-year with high friction exceptions to be granted by people other than 1st line sales managers.
- Retire quota in year 1. On a 50/50 comp plan with a 5x quota:OTE, commission is 10%. You can then SPIFF additional years; for example, 5% on year 2 and 2.5% on year 3 assuming the contract does not have a ‘termination for convenience’ clause. The SPIFF could come in the form of a quota credit multiplier but this has the disadvantage (from the company’s perspective) that it triggers accelerators earlier.
- Retire quota based on average ACV so that rep incentives don’t prevent ramp deals when those are in the company’s/customer’s interest.
- Train & certify reps on how to position and negotiate multi-year deals; don’t just leave things to chance.
- Compensating reps for multi-year deals (see here)
Customer Success:
- Ensure you have focused prioritization of multi-year accounts since CSM will tend to focus on accounts that closest to renewal.
- Include multi-year deals when calculating metrics used in CS compensation (retention, GRR, NRR) to align incentives such that CSM feel that are getting fairly paid for the work they do on these accounts.
Reference:
- KeyBanc Report (2019)

Opportunity Health Checks

No activity in the last x days (ex: 30)
(note: no inbound emails/replies or meetings held is more strict and better)
Days in stage of x times longer than that of closed won opps (ex: 2x)
Slipped deals
Close date in the past

B2B SaaS Sales Process Template

Sales Process Template in Google Sheets

N.E.A.T. Selling Sales Process Template from Richard Harris (Google Sheets)

Qualification & Deal Health Inspection

Qualification methodologies like BANT or MEDDICC/MEDDPICC can and should also be used for deal health inspection. While this can be done offline, I recommend tracking on your opportunity object in Salesforce. Often, qualification fields must be completed before advancing opportunity stages.