Cliff is an advisor and fractional executive for several high-growth start ups where he utilizes his expertise in all things GTM and RevOps, and an active leader of GTM in multiple communities.
With over 13 years of broad technology experience he has anchored GTM teams in SaaS and Service industries including consulting, regtech, network & communications, software, e-commerce, and supply chain. Having worked in both Fortune 20 and High growth startups, Cliff prefers the fast pace and the ability to deliver significant impact that comes with working in the start up space.
Outside of work, Cliff is married and lives with his wife and two small children. He keeps active playing soccer and hockey and volunteering with their local church.
Cliff, thank you so much for taking the time to chat with us today. We are so excited to learn from your expertise!
Thanks for having me, Trevor!
That’s a great question. I think one of the larger challenges that’s growing is change management as they scale. Having a great process that's documented and well-defined early on helps offset a lot. I personally would use Salesforce in order to future proof myself and ensure that I would have the historical data to make good data driven decisions in the future. Also the investors love it when you can show that growth trajectory.
Islin, I would determine what is the center of truth. You’re going to want to make sure that when you’re looking at your tech stack, you’re picking things that work within your budget and are complementary.
For me personally, that's always going to be Salesforce. I trust and know the reporting capabilities. As a startup I would say one Enterprise license of SFDC is far more capable when you account for the API access and the free tools available on Appexchange vs what you might see from Hubspot CRM.
Griffin, I look to see if I can capture the data points I know I'm going to need in 3-4 years, if I can create repeatable processes, and if I can easily add additional users without it breaking.
MRR & ARR are great. I’d also be looking at Churn and Net Dollar Retention. Cohorts on those clients monthly to look at renewal and usage.
I’m looking to grab volume metrics (MQL/SQL/Opps Created, CW) on the front end of the bowtie and the conversion rates that relate to those.
Churn and Retention are two of our favorites to crack!
It can be cost prohibitive to do so early on. The tool that I think does this really well and helps keep this moving without having to do a bunch of custom SQL is Immersa.ai.
Look at product usage vs expected, If you see usage trailing off that's a warning sign. I’m also a big fan of NPS as a leading indicator of where an account might be.
I love the simplicity of usage vs expected, especially as some companies are not mature enough to begin hiring in the Customer Success org.
In my experience, when you’re early, you should make sure that you’re taking that feedback loop and filtering it. What are the majority of users looking for? You can’t make your product be all things to all people. Focus on your ICP, your tier 1 and tier 2 clients and the things they need to iterate. Pass that info from Sales/CS to the product team continuously.
Early on I would put more emphasis on the middle of the bowtie, ie: CR3 and CR4. (conversion rate). I want to know more about the quality of my at bats before I scale the amount of at bats that my team is seeing. It's about figuring out the process before hitting the scale button. If I can help my team close at a 25% CW rate on 50 opps then scale the at bats we’re gonna do much better than if they are closing 5% and we throttle that early on.
I’m squarely on the Leads and Contacts side of this argument. I like having the clean delineation in CRM between those who have been qualified vs those who have not and should remain a lead.
Once we’ve qualified and that contact does not move forward in the sales process, that contact, or a lead who is not qualified should be fed into a nurture/drip campaign so nothing falls through the cracks.
Rhett, thanks for the question. It is completely possible that you don't need to buy anything new. To those teams on lower budgets, I would strongly suggest they go through the exercise of putting their processes down on paper and making sure that the process gives them the best chance for success. Dial in on your existing pipeline and the conversion rates there. Once you have that benchmark, look to see where you stack up against companies that have similar ACV and scope to better understand where you need to improve. Big changes in the org can come from incremental improvements across the pipeline - which is much easier than moving one metric by several standard deviations.
That's great advice, Cliff! Benchmarking can lead to so much opportunity for improvement.
Hi Kristina, how are things on the left coast? I'm a big fan of the 80/20 rule. Let's set up systems to tackle the majority and then look at things case by case until it becomes apparent that more automations should be built. CPQ, as you know, does a lot of this really well.
The gray area for me are items that you know you need flexibility on to be able to push something over the finish line.
Black and White are non-negotiables as you define them. Might be things like State law governing the agreement, the SLAs, renewal cost, increase for inflation...
Kristina, we're working through this currently at Miro and are trying to get to a point where Deal Desk is solely a strategic function and is not fixing quotes.
One thing that really helped us was mapping out our deals that came in the last 3 months and bucketing them into themes. Once we did this we automated as much as possible with the most common use case. We continued to peel off improvements from these buckets in hopes of getting our team closer to fully automated deal closure!
Exactly! We are in a very similar situation. It's too much to uncover ALL deals that have come in in the past. Unfortunately, there was no documentation here either... 👎 I think 3 months is a good timeframe to evaluate and bucket into categories.
Kristina, maybe go back longer to a critical event like a merger or whenever the last time new processes were introduced.
We are coming up on the top of the hour - Cliff, thank you SO much for chatting with us today and sharing your expertise with the community!
Also, thank you to Trevor for running point and for everyone that contributed!
Before we let you get back to your day, (and to that baby!) is there any last advice or tips you would like to share with the group before we sign off?
Think process and long term. Have a plan for where you are trying to go, then backwards engineer to get there.
Being rudderless in SaaS and business in general is a great way to burn out and endup nowhere.
True that! Definitely sound advice.
Thanks so much to Trevor, Erin, and the team here at RevOps Co-Op. This was a lot of fun!
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