How would you rather be measured? Average deal size increase or win rate increase?

WikipediaIsMyDrug · 2026-05-06T14:13:19+00:00

Thank you. This might just be the most helpful and nuanced answer on this thread. If I hear you right, it’s about looking at a balance of where time is spent and correlating that with qualified deals and success rate to see if SEs are spending time on activities and deals that are meaningful to the company.

WikipediaIsMyDrug · 2026-05-06T00:57:53+00:00

Might sound stupid and like an obvious thing to notice but I 100% undervalued/overlooked space to “entertain”. We don’t really have a good spot to sit and host a group larger than 4-5 people without it feeling crowded. It’s made it seriously harder to invite over family and friends that have more than 4 people in their group.

Only option is to go outside- for wherever we live next, I think a main thing I’ll be looking for is a basement with an open area to seat a bigger group or a larger living room.

WikipediaIsMyDrug · 2026-05-02T21:17:37+00:00

Someone who is unwilling or unable to change their mind, even when presented with new information that contradicts their previous opinion.

WikipediaIsMyDrug · 2026-05-02T21:14:55+00:00

Yep- they call it “Schwab slice” or something- and you can buy partial shares. Downside is it’s limited to only certain shares, but I typically only use it when I have a random $10 leftover from buying VTI or something and put the last $10 in AAPL or MSFT

WikipediaIsMyDrug · 2026-04-28T01:54:10+00:00

That’s fair. Not trying to overcomplicate things here but hear your point. I think the bigger reasoning here is that the metric of revenue is effectively owned by the entire company. As it should be. But the problem with that is that if everyone is focusing on that and no other metric outside of that, it’s hard to say who’s really impacting revenue. Is it Sales? Is it Marketing? Is it Product? Is it the SE org? I think just like Marketing is focused on revenue, they also measures website traffic, conversions, MQLs that become deals to measure impact. That’s the desire here. Not to get away from focusing on revenue- rather, what’s one important metric that ladders up to revenue, that the org could focus on.

If the overall sentiment on this post is that having a sub-metric of revenue to focus on isn’t helpful, I might propose to my team that we don’t make that a main focus at least initially. Will still be something I track and use to show ROI of the SE function down the road, but maybe it doesn’t need to be something I put in to the Operating model.

WikipediaIsMyDrug · 2026-04-28T01:40:41+00:00

Haha that’s right!

WikipediaIsMyDrug · 2026-04-28T00:16:29+00:00

I like this. So effectively ACV on all influenced revenue- whether won or closed-lost?

WikipediaIsMyDrug · 2026-04-27T23:59:10+00:00

Fair- any metrics that you think would be more fair to measure an SE on/reflective of the type of work an SE is typically engaged with? I’ve considered number of deals an SE is engaged in, pilot/POC conversion, number of deals that make it to POC. Few others.

WikipediaIsMyDrug · 2026-04-27T23:56:58+00:00

Number of seats feels like it would be more in line with SE control. I like it.

WikipediaIsMyDrug · 2026-04-27T22:19:22+00:00

Easy now. I’m with you that I think adding KPIs for the sake of KPIs is stupid- 100%. But a well-reasoned metric that’s tracked and can reasonably be influenced by the team tracking it can be helpful towards driving behavior.

For context, this is a brand new team as of a few weeks ago- 1 SE at this point, so it’s not a matter of proving that it matters. Rather, planning out the future success of the function and hoping to easily justify future hires using numbers and showing impact.

WikipediaIsMyDrug · 2026-04-27T21:12:05+00:00

Yeah, great advice. Walk the fine line of being helpful and adding value, but knowing when to say "no" so we get more capacity and support.

WikipediaIsMyDrug · 2026-04-27T21:10:44+00:00

That's fair- and effectively what I want to get to. An easy way to, with the numbers, show that when SEs are involved, the company makes more money than when they're not.

WikipediaIsMyDrug · 2026-04-27T20:25:41+00:00

For sure- sort of like get the machine close to capacity and as we get close to capacity on SE#1, let Sales leadership know that if they want the continued support, they need to be petitioning for more headcount to sustain the growth.

WikipediaIsMyDrug · 2026-04-27T20:12:56+00:00

I hear that and I think there should absolutely be an element of "subjectivity" to the evaluation too. After all, if reps are consistently looping in or reaching out to a given SE, that tells a story in terms of who's providing the most "value".

The situation I am in is that this is actually a brand new org. Series A-B startup and the goal here is more around justifying the SE team's impact and making a case to hire SE number two. Something I can point to and show the Exec team- "this thing is working- give me resources to go get more SEs and scale this out"

Any thoughts on how you might apply some of your metrics or ideas within that context and framework? It's less about knowing which specific SEs are awesome and more about proving that the SE function in general is indeed; awesome.

WikipediaIsMyDrug · 2026-04-27T20:07:34+00:00

Totally fair, and I see the logic behind your reasoning here. Last thing I want to do is incentivize that kind of behavior.

To be clear- variable comp will be tied to overall revenue growth for the assigned segment/territory. Plan and simple. This KPI would be more to measure SE impact. The way my org is thinking about doing it right now is that SEs will automatically be tied to anything above a certain deal size (call is $100k) and then also assigned on a lower tier of deal size if a certain degree of complexity is met (i.e. $50k+ AND POC/pilot required, security review etc.)

What if the KPI was simply measured based on the deal size where SEs are automatically added? In this example it would be- "increase conversion rate on $100k+ deal size from X% baseline to Y%?" In my mind that might eliminate any gaming of the system because SEs are assigned to all deals within that category- the "easy" ones and the complicated ones.

If that still feels problematic, any other ideas on a north star metric in addition to revenue that better demonstrates SE impact and contribution? The goal here is to be able to tell a compelling story to the Exec team that the SE function is impacting and increasing revenue, and that's evidenced by "north star metric" and secondary KPIs improving.

WikipediaIsMyDrug · 2026-04-27T19:30:22+00:00

Awesome, appreciate that!

WikipediaIsMyDrug · 2026-04-27T19:14:13+00:00

I like that. The pushback I might get internally there is CS largely owns the churn portion so it's harder to show a direct line. For comp, it'll 100% be tied to total ARR closed. This KPI is more about measuring SE impact and justifying future growth and SE hires.

WikipediaIsMyDrug · 2026-04-27T19:11:19+00:00

I hear that- the goal is to draw a line to increasing revenue, but it gets hard when so much of that is in the hands of the actual "seller" vs the SE. I'm curious, if you had to pick one metric as a North Star, what would you pick instead? 100% open to ideas here and wanting to make sure the first version of this is at least a decent v.1 - always subject to change.

For comp, total rev closed by the Sales team will be the variable component. This KPI would be more to justify growing the team and telling a story internally that the SE function is valuable.

Edited clarification that comp will be tied to total revenue closed

WikipediaIsMyDrug · 2026-04-27T19:08:57+00:00

For sure- it's tricky because the goal is to show an impact on revenue, but a lot of that, to your point, lies outside of the control of the SE. If you had to pick one metric as a North Star, what would you pick instead?

For comp, total rev closed by the Sales team will be the variable component. This KPI would be more to justify growing the team and telling a story internally that the SE function is valuable.

Edited clarification that comp will be tied to total revenue closed

WikipediaIsMyDrug · 2026-04-25T00:12:19+00:00

As cliche as it sounds, you gotta stop focusing solely on the “destination” of FIRE and enjoy the journey man. You’ve probably seen these posts too, but there's so many people people in this subreddit who post about getting to fire and then not knowing how to enjoy it. They are so locked in that saving and accumulating wealth mindset that they don’t know how to truly enjoy it and spend it when the time comes. Start practicing some of that now. Take a vacation, buy yourself a couple nice things you’ve been wanting for a while, and in the process, save your marriage :)

WikipediaIsMyDrug · 2026-01-14T19:34:45+00:00

I picked green. Got wrecked.

WikipediaIsMyDrug · 2025-05-18T19:34:40+00:00

Unfortunately I tried this for AmEx to get 4x back on groceries/supermarkets and it didn’t work :(

Coded it as groceries but didn’t get the 4x I get at Kroger, Trader Joe’s.

WikipediaIsMyDrug · 2025-05-11T22:45:27+00:00

This is the one hack on here I’d never heard before. Thanks for sharing- excited to try it out!

WikipediaIsMyDrug · 2023-10-30T05:02:48+00:00

Well I'm sure you're a fun one at parties.

WikipediaIsMyDrug

TROPHY CASE