How do you navigate sales enablement at a startup that serves multiple sectors of the market and has limited resources?

Are you perhaps stretched too thin with multiple/various buyers. Do you need to do a buying persona exercise vs accelerated sales enablement?

Sometime Sales Enablement is over thought. Ultimately it is about facilitating/suppporting the selling process. If you are pursuing many varied buyers, what is the lowest common denominator that covers them and work backwards. For instance, can you get away with the same proposal template? Can sellers be trained at the same time? Is there a common use case? In the abesence of this, simply aling yourself with a few sales leaders and take it from there. 

Prioritize the top sectors - pick 2-3 and then build a playbook you can replicate. I would also say, set realistic expectations with your GTM teams so they understand your limited bandwidth and be clear on what you can get to and what you can't. Work with your sales and CS leadership in terms of focus and priority (product training, onboarding, systems training, etc.) so that there's clear alignment as well! 

If you have limited resources, the only thing to do is to prioritize. You cannot try to do it all at once, so focus on the ones that will make the biggest impact. 

For instance, if you are moving into new sectors - chances are you already have existing enablement materials for existing sectors - so for a quarter or two, you can potentially just focus on the basic list of deliverables you need to get the sales team selling into the new markets.

Figure out what is doable with the resources you do have and then focus on a few things at a time!

Great question. As someone who's worked in a number of startups, I can definitely relate to the pain of trying to do too much at once.

In terms of prioritizing your enablement development/rollout across sectors/personas, here's how I think about it:

1. ARR talks: Run the numbers on your serviceable addressable market. Basically, look at the sector population and your average deal size or customer lifetime value to stack rank the opportunity by potential $$.

2. Ability to deliver against customer pain: It's tempting to push forward based on aspirational use cases, but spend the time mapping your ARR opportunity to how customers are actually using the product. Prioritize the audiences that have the most straightforward path to value.

3. Once you have the potential $$$ and ability for your product to deliver, it becomes more of a straightforward discussion for enablement priorities with your sales leaders. Start with the most lucrative/obvious use case, roll it out to sales teams, and use the customer insights to improve the next sales play* you develop.

*In terms of the enablement itself, I'm a big fan of modeling out expected ARR based on usage or firmographic data so that account executives can prioritize whether it's worth their time to run the play. In addition, less is more—keep it really simple to follow and provide just the critical information they need.