SaaS ENT Sales Pipeline Weekly Management KPIs: CXO?guide

Every SaaS CXO has its way and practice of managing the Sales pipeline. Nowadays, all modern CRMs offer “built-in” dashboards and a certain set of KPIs to track. Moreover, multiple CRM add-ons (e.g., InsightSquared ) can give you a pre-built set of pipeline dashboards to track pipeline changes as often as you want?—?even daily.

But what are the requirements for weekly pipeline reviews? What kind of discussions and data do CXO leaders need to run weekly to drive the right Sales team behavior and keep the team accountable?

Here are my top 5 objectives for meaningful Pipeline Health discussions (filtered by AE (Sales team), Product (or product group), and geo):

• 1. Set the Gold Standard: Define a “gold standard” for the opportunity journey (AKA “funnel health”) at every sales stage. It’s like creating the perfect recipe for sales success?—?except instead of secret ingredients, it involves entrance and exit requirements captured with CRM Opportunity fields tailored to your sales process. That also should include expected time (days) at every sales stage, CR (conversion rate) % from sales stage to sales stage, etc…
• 2. Individual Pipeline Health Plans: Give each Account Executive their own personalized “pipeline health” plan. It’s like crafting custom workout routines for your sales team?—?except instead of dumbbells, it involves weekly new opportunities generation targets and weighted pipeline expectations. It should include weekly new opportunities generation targets, weighted pipeline expectations (# and the total value of opportunities at the high sales stages), and pipeline dynamics (# of opportunities at particular sales stages, including “Closed Won”) expectations.
• 3. Map to Gold Standards: Weekly mapping of all active opportunities to known “gold standard” parameters will give your Sales Leader an immediate set of Red Flags to look at. It’s like having a treasure map, except instead of buried treasure, it leads you to sales success.
• 4. Pipeline Dynamics: Keep track of the weekly flow of your pipeline, because just like a rollercoaster, you want to make sure you’re always heading in the right direction?—?up!
• 5. Weekly Activities: Keep tabs on your team’s activities to ensure they’re staying engaged with prospects. After all, silence and time usually kill all active opportunities?—?kind of like a relationship with a ghost.

Understanding the objectives of pipeline discussions, let’s delve into the essential Enterprise SaaS (Direct Sales) KPIs to track. These are grouped into several sections.

1. Your weekly Forecast update (see my older blog on forecasting techniques for more details). It’s a pretty straightforward exercise:

• Take a current week snapshot of opportunities at higher stages (usually at the “POC” stage and above).?
• Discount all opportunities that failed to meet “funnel health” criteria.
• Add “shadow pipeline” value (mind the remaining weeks left in your current fiscal quarter).
• That is your current quarter “commit” forecast.

2. Weekly Pipeline dynamics. Your first report to look at is a weekly pipeline snapshot by sales stage (opportunities amount and total value)?—?with WoW changes. I always track it by AE, product group, and geo. It makes sense to look at the following GREEN, YELLOW, and RED flags here:

• GREEN: pipeline growth (# and value of opportunities elevated to higher stages).
• RED: “Closed LOST” opportunities?—?always run a weekly discussion on the core reasons, and share complex cases with engineering and development teams.
• YELLOW: opportunities that are stuck at the particular sales stage longer than average (7 days+).

3. Weekly activities. Activities are critical to monitoring your Sales team’s contribution and their ability to drive active discussion with prospects. Silence and time usually kill all active opportunities, so an experienced Sales leader is always able to catch any stalled opportunities early enough and help the team. Same as above, you have to track WoW changes (by AE, product group, and geo).

What are the GREEN, YELLOW, and RED flags here:

• GREEN: opportunities are active and communications are within target activity levels by sales stage.
• GREEN: # of newly created opportunities (and qualification calls) added (and elevated to the next stage) is meeting the target level.
• YELLOW: 7days+ communication drop from the prospect side (by sales stage).
• RED: “radio silence” on the prospect side for 2weeks+ with several contact attempts from the opportunity owner (I always ask to make calls & social media messages apart from traditional e-mail communications).
• RED: low new opportunities activation performance?—?way below expectations.

4. Weekly “POC (managed product trial)” sales stage opportunities review. Running a separate weekly call dedicated to Enterprise-size POC stage opportunities allows for a deeper dive into technical issues. The main reason is a Sales Engineering (or Solution Architects) team involvement?—?so you can dig deeper into POC technical (deployment and usage) issues.

Apart from the technical issues discussion, there are still similar GREEN, YELLOW, and RED flags here:

• GREEN: POC stage opportunities with completed milestones (GTM specific) and within the required timeframe.
• YELLOW: POC stage opportunities?—?missed milestones dates.
• YELLOW: POC stage opportunities without opportunity amount.
• RED: POC stage opportunities?—?without deployed product.

5. Individual pipeline discussion (at AE or particular Sales team level)?—?with WoW dynamics.

Depending on your Sales team size, I suggest running individual pipeline discussions with your top sellers and team (geo) leads. Apart from traditional opportunity attributes (name, size, amount, owner, sales stage, age in days, age in days at current opp-ty stage, forecast category), I suggest to track the following additional attributes:

• Missing (incomplete) CRM fields and stage.
• No prospect communication for the last 7+ or 14+ days.
• 7+ days at sales stage above GTM average.
• Individual (team) CR% deviation from prospected GTM benchmark.

So, as a Sales Leader, you have to build your weekly Pipeline routine (AKA Rhythm Of Business (ROB)) and follow the logic described above. Please make sure that all necessary reports will get automated, so your team will not waste any time preparing for weekly calls and stay focused on sales conversations and activities.

I have experience with Tableau and PowerBI as “dashboarding” tools, and would recommend PowerBI as a more flexible and affordable one.

Remember that as CXO, you are in charge of your GTM design?—?including sales stage criteria and sales automation/reporting tools. Don't leave it to your sales team, you want them selling rather than pulling and building reports for you. You also should rely on a single “source of truth”?—?your CRM.

Stay tuned for more insights on monthly/quarterly ENT SaaS KPIs and Partner-led business KPIs in future blogs.

Happy selling, and stay tuned for the next Sales Insights!