u/EnonymousAmigo

for 2 years we ran standard linkedin outbound.

connection request.
follow up.
“just bumping this.”
“wanted to circle back.”

the usual SaaS SDR playbook.

reply rates slowly died every quarter.

we rewrote templates constantly thinking the copy was the problem.

turns out the bigger problem was that prospects instantly recognize sequence structures now.

we tested something different this quarter:
instead of templates with placeholders, every message was generated uniquely based on the prospect’s profile, activity, and company context.

same ICP.
same offer.
same market.

reply rates went from ~3% to ~17%.

the weird part:
volume actually went DOWN.

but conversations became much higher quality because messages sounded like they came from someone who actually understood the person’s role.

biggest lesson:
most outbound SaaS teams are optimizing sequence copy when the actual problem is that buyers mentally filter anything that feels like a sequence.

curious if other teams here are seeing the same thing with outbound in 2026.

been building a side project after work for almost a year now

classic story. designer learns to code, watches too many startup videos, decides hes gonna “build in public” and change his life

the project itself was actually useful. i built Kakiyo because i was tired of manually doing linkedin outreach every single day for freelance clients. originally it was just supposed to generate better personalized messages so i could stop rewriting the same thing over and over

but then i got carried away

analytics dashboards
glassmorphism UI
animated charts
activity heatmaps
a settings page with like 40 toggles nobody on earth needed

i spent an entire saturday redesigning the onboarding button hover animation. not joking

finally launched it properly last month

know what users cared about?

whether the messages got replies

thats it

one guy literally emailed me saying “bro i dont care about the dashboard just tell me if this thing books meetings”

another user thought half the features were fake because he never clicked them once

the real fuck up happened when my server bill randomly spiked because of all the unnecessary analytics garbage i added trying to make the product look “premium”

ended up spending more money tracking user behavior than actually improving the thing users wanted

so i stripped almost everything down over one weekend out of frustration

simpler UI
less settings
bigger text
just focused on whether the outreach worked

and somehow thats when people actually started paying

turns out nobody wants a spaceship dashboard if the core product sucks

would have been cool to realize that BEFORE wasting 6 months pretending i was the next Steve Jobs

TL;DR: spent 6 months overdesigning my app Kakiyo with useless features nobody cared about, nearly burned money on pointless analytics, and learned users only care if your product actually solves their problem

so i built this tool called Kakiyo for linkedin outreach because i was tired of writing cold messages manually every day

the whole point was making AI generated messages not sound painfully robotic

which worked a little too well apparently

couple weeks ago i matched with someone on hinge and we started talking. conversation was going fine at first but i was exhausted from work and honestly terrible at texting

meanwhile Kakiyo was sitting open on my second monitor because i had been testing conversation prompts earlier

you can probably see where this is going

as a joke i pasted one of her messages into the AI to see what it would reply with

the response was annoyingly good

like thoughtful. funny. actually engaging

so naturally i copied part of it

then another

then somehow the AI was carrying like 70% of the conversation while i sat there feeling progressively worse about myself

three days later she literally says:
“its really nice talking to someone who communicates this clearly”

i almost closed my laptop permanently

the real disaster happened when we met in person

because apparently real life me does NOT sound like polished AI-assisted text me

conversation was awkward almost immediately. she kept waiting for these deep insightful responses and instead got me nervously talking about figma plugins and iced coffee

at one point she literally asked:
“you seem different over text?”

i wanted the earth to consume me right there

there was no second date obviously

now every time i work on Kakiyo i remember that i technically got outperformed by my own product in a real human interaction

which honestly feels deserved

TL;DR: built an AI messaging tool called Kakiyo, jokingly used it during a dating conversation, accidentally made myself seem way cooler than i actually am, then completely failed to live up to it in person

this happened last week and im still not sure whether to feel impressed or unemployed

for context, ive been doing freelance web design for about 3 years. most of my work comes from linkedin outreach and referrals. the problem is i absolutely hate outreach. like genuinely hate it. writing the same “hey saw your company and thought we should connect” messages every night made me want to throw my laptop across the room

a friend convinced me to try Kakiyo a few months ago. its basically an AI thing that helps handle linkedin outreach conversations. i was skeptical because most “AI sales” stuff sounds like a robot having a stroke

but it actually worked weirdly well

anyway last week i got a notification while eating dinner that a prospect booked a discovery call through one of the conversations. cool. normal

then the guy replies again before the meeting and says:

“honestly your outreach was refreshing. most people pitch immediately but whoever handled this conversation actually understood our redesign problems.”

except i didnt handle the conversation

the AI did

so now im sitting there staring at my phone realizing a machine apparently understands my own service better than i do

it gets worse

we jump on the call the next day and the prospect starts referencing points “i” brought up earlier in the chat. except i have NO idea what hes talking about because again, the AI said it

i literally had to scroll through the conversation during the call pretending i remembered everything

somehow closed the project anyway but the entire time i felt like a group project student who didnt do the reading

the worst part is the client later emailed saying “looking forward to working with you guys”

there are no “guys”
its literally just me and a confused laptop

TL;DR: used an AI outreach tool called Kakiyo to help with linkedin conversations, forgot it was handling replies, got on a sales call completely unprepared while the client thought i was some genius strategist