Gašper Š. Honestly, I’d stop thinking about “channels” for a second and focus on where the pain becomes operationally expensive. RFPs and security reviews usually don’t become painful at 5 questionnaires/month. They become painful when: -enterprise deals start stacking up -sales cycles slow down -SEs and founders get pulled into repetitive work -procurement becomes a bottleneck So if I were you, I’d probably narrow aggressively toward companies already feeling that operational drag instead of broad outbound. A few things I’d test quickly: -Trigger-based outbound around hiring/security/compliance motions -Partnerships with vCISO / compliance firms already inside the process -Messaging around revenue slowdown and deal friction, not “AI automation” -Very tight wedges by buyer type instead of generic ICPs Most teams I see struggle because they try selling the tool instead of attaching themselves to an expensive operational bottleneck.
Appreciate the thoughtful response 🙏 I think you’re probably right that we’ve been positioning too much around “questionnaire automation” instead of the operational pain around slowing enterprise deals and draining SE/compliance time. Curious about one thing regarding the trigger-based outreach idea - would you approach that through LinkedIn and target multiple people from the same company once you detect signals (enterprise hiring, SOC2/compliance motion, etc.), or would you go through some other channel entirely?
I'd go linkedIn first and test for signal on a per-persona level. Narrow down then step by step scaling up. This way you are not get shadow banned and your message hit it's mark. The influencer/ABM-style strategy you're describing only works when you have language/market fit with each persona in the buying center. Doesn't take too much time, you can do compressed sprints (3-5 days each), get signal, and ramp from there. Once the 'system' is in place, do that again and again for target audiences.
Gašper Š. you should check out this webinar - https://luma.com/gps5on59 (I know Oleg from Extrovert) and I can also make an intro to founder of gelee.ai - she's a master at LinkedIn outbound.
Thanks, I’ll check the webinar. I think at this stage we first need to get our hands dirty again before we try scaling it with tools.
Yes and no, IMO. Might be worth a call regardless. She got one of my clients half a million impressions and started small on outbound. Regardless, my first msg stands. Go deep on your buyer and targeting… will save you a ton of headaches (and cash). Best o luck
fantastic advice JCB!
