Revenue Operations

Building, Scaling, and Changing your RevOps Org with Cliff Simon

We chatted with Cliff Simon , Vice President of Sales & Revenue at Carabiner Group about RevOps, how to create a recurring revenue engine, how to design a RevOps tech stack, and more! This was a treasure trove of actionable information and we’re grateful for Cliff’s time and energy. 


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.


Interviewing is Trevor Greyson, GTM BizTech at Miro and Co-founder of the RevOps Co-op.


Trevor Greyson (RevOps Co-Op)

Cliff, thank you so much for taking the time to chat with us today. We are so excited to learn from your expertise!

 

Cliff

Thanks for having me, Trevor!

 

Trevor Greyson (RevOps Co-Op)

As we focus the conversation today on recurring revenue and revenue systems, let’s start at the beginning for a bootstrapped company who just began selling somewhat successfully and now needs to figure out how to operationalize their selling strategy. We hear about Hubspot and Salesforce being thrown out as starter packs to procure and get companies up and running. With your experience, do you recommend a revenue system such as these two to start? Or where do you point founders in need of direction with this new exciting problem?

 

Cliff

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 Munisteri

How do you choose between HubSpot and Salesforce as a startup?

 

Cliff

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.

 

Trevor Greyson (RevOps Co-Op) 

Great insight, Cliff!  When consulting for these small companies how do you focus the conversation on the process of recurring revenue prior to jumping directly into systems?

 

Cliff

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 Lee

What are core points you tend to take into account when choosing your first system to help scale?

 

Cliff 

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.

 

Trevor Greyson (RevOps Co-Op)

What are some of these data points you feel are imperative for startups to nail? ARR, MRR, TCV?

 

Cliff 

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.

 

Griffin Lee

What are those data points you're looking for? Anything in particular?

 

Cliff

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.

 

Trevor Greyson (RevOps Co-Op)

Churn and Retention are two of our favorites to crack!

PLG and Product usage is the topic of conversation everywhere these days. Do you recommend startups bring this product usage data into SFDC at an early stage of growth? Which metrics do you recommend tracking that end up relating back to repeatable recurring revenue?

 

Cliff

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.

 

Trevor Greyson (RevOps Co-Op)

I love the simplicity of usage vs expected, especially as some companies are not mature enough to begin hiring in the Customer Success org.

  

Patrick Monnot

Cliff, thank you for your insights! What have you seen as being the most efficient approach to get your first 100 paying users and how do you think about balancing product feedback and revenue generation?

 

Cliff

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.

 

Trevor Greyson (RevOps Co-Op)

As we think about recurring revenue engines, you spoke a bit about MQL/SQL earlier, but how much emphasis do you place on top of funnel metrics and how do you recommend founders begin tracking these data points?

 

Cliff

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.

 

Griffin Lee 

On the topic of top of funnel ...Do you think "leads" should be washed away completely in your CRM and the use of contacts implemented soley? And why?

 

Cliff 

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. 

 

Trevor Greyson (RevOps Co-Op) 

How do you track users who qualify or hand-raise more than once? Do you append the “Leads to Contact” record?

 

Cliff 

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 Hartsfield (Vertify)

Hi, Cliff! A bit redundant to above, but I’ve heard someone say the answer to what systems to leverage could lie within what you have, not new tech. How do you advise teams with low budgets/in start ups who obviously want to be dialed in on revenue focused activity and creating an ideal buyer’s journey? Should they bite the bullet and invest in tech or dial in harder?

 

Cliff 

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.

 

Trevor Greyson (RevOps Co-Op)

That's great advice, Cliff! Benchmarking can lead to so much opportunity for improvement.

 

Kristina Jobert

On the topic of deal desk strategy - any tips on managing complexity especially with non-standard deals? What factors into the definition of non-standard? What are areas that should always be kept as "gray area" versus what should be streamlined to be a more definitive black/white process?

 

Cliff 

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...

 

Trevor Greyson (RevOps Co-Op)

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!

 

Kristina Jobert

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.

 

Cliff

Kristina, maybe go back longer to a critical event like a merger or whenever the last time new processes were introduced.

 

Erin O'Neill (RevOps Co-op)

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?

 

Cliff

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.

 

Erin O'Neill (RevOps Co-op)

True that! Definitely sound advice.

 

Cliff 

Thanks so much to Trevor, Erin, and the team here at RevOps Co-Op. This was a lot of fun!


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