Dan Oakes on AI Lead Generation and Signal-Based Prospecting
About Dan Oakes
Dan Oakes is the Founder of Startup Sales Consulting. In this conversation, he shares approaches to AI lead generation, signal-based go-to-market plays, and customer discovery that help sales teams improve prospecting workflows.
Episode Notes
Key moments from this episode
Dan Oakes, Founder of Startup Sales Consulting, joins Tailwind to explain how sales teams can use AI for lead generation with a clear strategy underneath it. He identifies three common mistakes: buying tools without defining outcomes, spending AI tokens on tasks traditional software already automates, and letting reps build overlapping workflows without clear ownership. Dan recommends mapping who to reach, when to reach them, and how before adding automation. Start with one frequent, high-confidence trigger that is easy to find, prove the outreach with a willing rep, and reuse the downstream enrichment and sales engagement workflow. The conversation also explores how customer discovery reveals why buyers enter the market and how teams can translate those changes into observable prospecting signals. His closing principle is simple: make outreach effective before using AI to make it more efficient.
Takeaways
- Define the strategy before buying AI tools: identify the outcomes, target accounts, timing, messaging, and ownership of each prospecting play.
- Use AI where research or judgment adds value. Keep repeatable delivery, enrichment handoffs, and other clear if-then tasks in existing automation where appropriate.
- Start with one trigger that occurs often, has proven messaging, and is easy to find. Pilot it with a willing rep and validate results before expanding.
- Reuse the downstream workflow across plays, adapting contact selection when a company-level signal calls for multiple champions or an individual signal calls for one person.
- Ask recent customers why now was the right time to buy, find shared changes in their businesses, and look for observable signals that reveal similar situations elsewhere.
Key Moments
- 0:20
Three common mistakes in AI lead generation
Dan explains strategy gaps, unnecessary token spending, and duplicate rep workflows without clear ownership.
Read transcript at this moment - 4:08
Use AI for judgment and software for repeatable tasks
The conversation separates AI research and prioritization from deterministic tasks and established sales engagement delivery.
Read transcript at this moment - 8:14
Map triggers, ownership, and the downstream workflow
Dan starts from first principles and maps go-to-market plays from signal sources through enrichment and outreach.
Read transcript at this moment - 12:41
Start with one high-confidence play
Pick a frequent trigger with proven messaging and an easy build, pilot it with a willing rep, and reuse the workflow as the team expands.
Read transcript at this moment - 22:15
Find bespoke signals through customer discovery
Recent customer conversations reveal buying changes and observable signals that can make outreach more relevant than crowded generic triggers.
Read transcript at this moment - 29:13
Make outreach effective before scaling efficiency
Dan closes with a simple priority: send good outreach to the right people, prove it works, and then use AI to scale its efficiency.
Read transcript at this moment
Transcript
0:02 Dan, as I was saying, I was reading
0:03 through uh uh the the bullet points that
0:06 you had. I couldn't agree with more with
0:08 like kind of your approach. Um but I
0:10 think a great starting point is, you
0:12 know, you're talking about mistakes that
0:13 folks make when they're using AI for
0:15 lead generation. Do you mind
0:16 highlighting some of those just to
0:18 begin?
0:20 >> Yeah, there's a few that most mistakes a
0:23 few categories that most mistakes I see
0:25 fall into. And the first one is they
0:28 they buy these tools or give tools to
0:31 their folks. They don't really have an
0:32 underlying strategy.
0:34 >> I think we all remember when the AI SDRs
0:37 became the the big craze in Silicon
0:41 Valley and beyond. And I think very few
0:44 folks had a lot of success with those
0:46 because
0:48 >> they didn't really have a underlying
0:49 strategy behind it. They just took the
0:51 tool, spent a little bit of time, just a
0:54 very little bit of time and energy and
0:55 let it do its own thing. And that that
0:59 was successful because they didn't
1:01 invest the time upfront to clearly
1:03 define what are the outcomes that they
1:05 want to do, what do they need the AI to
1:07 do, and what's really just a
1:09 deterministic workflow that they don't
1:11 necessarily need AI that the tool
1:14 uh can can do very well. So that that's
1:16 one category, AI with not not a lot of
1:19 strategy. Another category is
1:23 burning too much money and token spend
1:27 on things that you don't really need to.
1:29 Uh, one of my clients that I worked with
1:31 earlier this year, one of their SDRs was
1:34 spending
1:36 I can't remember the exact dollar like
1:38 $50 to $100 per week on this one AI
1:41 workflow to find what resulted in like a
1:45 couple qualified leads per month. And
1:49 the the reasoning behind that is that
1:52 they were over complicating it and using
1:55 LLMs for a lot of things that are really
1:58 just deterministic workflow. Software is
2:01 great at automating things and AI is
2:05 good for making a little bit of
2:06 decision-m and you don't need you just
2:08 want to make sure that you use the the
2:11 right tool for the the right workflow.
2:15 Mhm.
2:15 >> Um,
2:17 and the the third main problem I see is
2:21 there's no overall
2:24 structure or strategy behind on a
2:27 company level around who's doing what.
2:30 And so what I mean by that is I see a
2:33 lot of companies they they are doing one
2:36 thing great which is allowing the the
2:39 people on the front line the individual
2:41 contributor SDR and AEES to have claude
2:45 or whatever your AI tool is but there
2:50 there's just no structure or guard rail
2:52 or I like to use what the c consultants
2:57 call a mei framework meaning mutually
3:00 exclusive, completely exhaustive
3:02 framework around just somebody mapping
3:04 out that here are all of the possible
3:09 if if you're using it for lead genen,
3:12 here are all the possible types of leads
3:15 in our TAM and here's clear ownership
3:18 around which rep is doing which workflow
3:21 or covering which type of leads. And
3:23 then so if you don't have one
3:24 centralized person whether that's a
3:26 sales leader or somebody on the rev ops
3:28 team governing that then you're then
3:30 what I've seen is
3:33 uh the reps spending too much time
3:36 building this the duplicative tools
3:39 which isn't a great great use of uh time
3:41 and resources and also targeting this
3:44 the same folks with the same plays and
3:47 so those are the top mistakes that that
3:49 I see. So for maybe like the less
3:52 technically minded, when you say like,
3:54 hey, somebody's using an LLM for
3:56 deterministic, you know, work, you know,
3:59 how would you break that down in like
4:00 super layman terms so that like somebody
4:03 hearing that like idea for the first
4:04 time could understand that pretty
4:06 quickly?
4:08 >> Yeah, I'll break it down. But the
4:09 analogy that I would make is using a
4:12 flamethrower to
4:14 >> just need a a fly swatter.
4:16 >> Yeah. And so a specific example of that
4:21 would be using a tool like Claude or
4:25 Chat GPT to
4:29 send uh to like to send an email for
4:33 example when when really you already
4:35 have a sales engagement platform that
4:37 just follows very clear if then
4:39 statements that it just runs it runs one
4:43 line of code instead of prompt ing an
4:46 LLM to consume a bunch of tokens to do a
4:49 very simple task that's automated that
4:53 for for decades SAS software has been
4:55 doing the these automated tasks versus
4:58 running an entire new prompt through an
5:01 LLM that that consumes more tokens.
5:03 >> Yeah. And and for somebody who's looking
5:06 at this and thinking like, okay,
5:09 that's a that's a straightforward one.
5:11 Like we've had these tools where they've
5:12 been able to just automatically insert
5:14 somebody's name into like the body of an
5:16 email saying hi person's name
5:18 automatically entered. You don't need
5:20 Claude to rewrite an entire email just
5:22 to put in that name. Um what are some of
5:24 the other basic examples that people can
5:26 start kind of wrapping their head around
5:28 where you know deterministic is totally
5:30 plausible. It works. It might even be
5:32 more effective and less like prone to
5:34 error because it's not going to
5:35 introduce an LLM's variability.
5:38 >> Yeah. So [clears throat]
5:41 I actually think that sales engagement
5:43 platforms are great.
5:45 >> Yeah.
5:46 >> And teams should be using them. And
5:50 you know outreach sales loft they took
5:53 off uh you know however many years ago
5:55 in the in the 2010s and that was all
5:58 deterministic
5:59 software. And I I still think that
6:04 th those many of those same things still
6:07 should be used today that getting
6:10 getting meetings for example it like
6:12 nothing's really changed with how people
6:14 buy like and are excited to get uh a
6:17 meeting
6:18 >> and you you can reach people the same
6:20 way. You it's really just sending good
6:25 information, good messaging to the right
6:27 people at the right channels. So, I
6:30 think teams can still use these sales
6:32 engagement platforms for the final
6:35 delivery. Um, it's just AI has its place
6:38 upstream of that to figure out and
6:41 prioritize who to reach out to
6:44 >> and when. and the
6:49 um yeah, so the the deterministic so you
6:52 don't you don't need to use an AI to
6:55 both figure out who to reach out to and
6:59 craft a new sequence every single time
7:01 and craft messaging in that sequence and
7:04 figure out which tool to use to
7:07 uh to send the email to uh do all these
7:11 other things. Um, it's like use the AI
7:14 for the the stuff that requires a little
7:16 bit of judgment and then spend the time
7:18 and energy up front to map out what the
7:21 deterministic workflow is like and then
7:23 and then just map it the data flow
7:26 downstream like that.
7:27 >> Yeah. Yeah. So like it seems like the
7:30 rule of thumb is if like any of these
7:32 sales engagement platforms, Apollo,
7:34 Outreach, you know, Sales Loft, if they
7:36 were doing it in the 2010s, it don't
7:39 don't apply LLM to it. they already have
7:41 it figured out. There's no no ad for
7:43 that. Um, and then I think, you know, I
7:46 think you're just alluding to kind of
7:47 like how to fix the problem of like the
7:49 mistakes, which is to start with
7:51 mapping. Um, and then kind of figuring
7:54 out what you're trying to do before just
7:55 throwing AI on top of that. Um, so if we
7:58 have those mistakes or if you kind of
8:00 have a sales leader sitting here and
8:01 going, "Oh, I kind of I just heard what
8:04 we're doing and I just felt this pain."
8:06 uh what would you recommend as like a
8:07 first step um to start getting out of
8:10 that pain and into an effective use of
8:12 it?
8:14 Yeah, the I think the first step is just
8:17 mapping out
8:19 what I like to start from first
8:21 principles with everyone I work with and
8:24 map out what excellent looks like, what
8:26 what good looks like and what you want
8:29 your reps to do and
8:32 >> um like who should they be reaching out
8:34 to when should they be reaching out to
8:37 them and and how. And so what's probably
8:43 going on whether sales leaders are
8:46 working with teams that have territories
8:49 but
8:51 certain rules of engagements or named
8:53 account lists and the reps are using AI
8:57 to to help out with prospecting.
9:00 They're they're probably the reps are
9:02 probably using AI to
9:06 um
9:08 just like create a bad a lot of bad
9:11 messages. They're probably using AI to
9:13 to do the the endto-end workflow. So I I
9:16 would break it down into
9:18 um what are reasons why people buy our
9:22 product? What is a really good signal?
9:25 What is a good positive trigger that we
9:28 can find that that's a a good reason for
9:31 us to reach out to uh this company and
9:35 what is good messaging that we already
9:37 know works that when we see this trigger
9:40 and this message um if we just deliver
9:43 that message whether it's email call
9:46 LinkedIn we know that generates meeting
9:48 I I would start with that and just map
9:50 out and be creative because AI has a lot
9:54 of really good capabilities to find
9:55 information, find these otherwise really
9:58 challenging to find triggers that it
10:00 would take many hours of research
10:02 before. So, map out all of these
10:04 different triggers that you you want you
10:06 want your team to be reaching out to uh
10:11 people with and have some general
10:15 messaging for each one of these
10:16 triggers. And then I I I would assign
10:20 clear ownership to um I like to call
10:23 each one of these trigger based outreach
10:25 a go to market play. So have clear
10:27 ownership around who owns what specific
10:29 plays so that you know it's getting done
10:32 on a weekly basis or depending on the
10:34 the trigger a monthly basis. But it's
10:36 it's a very very clear onetoone
10:38 ownership and and just to make things
10:40 equitable. You can rotate those between
10:43 either your SCR team every every week or
10:45 every month just to so there's no bias
10:47 in hey this this play is getting more
10:50 leads for than than the other. But um
10:52 yeah the first part is like map out all
10:54 of these uh different different triggers
10:56 and plays. figure out what are the
10:58 databases that
11:00 um that you're going to get this
11:01 information that whether it's a
11:04 newsletter, whether it's scanning
11:05 LinkedIn, whether it's uh hiring
11:07 updates, whether it's uh I I I've made
11:11 built some plays based off of new SEC
11:13 filings. just figure out what the
11:14 database source is, then build the AI
11:17 agentic capabilities to scan those
11:21 sources on a regular cadence and then
11:24 map out the the downstream funnel from
11:27 there. So, it's typically you're going
11:28 to find the for each single play, do the
11:31 same. It's the same pipeline, do the
11:32 same thing. It's use the AI to find the
11:35 the trigger or signal. Then you you have
11:38 to figure out um you're probably going
11:41 to put that information in some kind of
11:43 database to say okay here's the company
11:44 exhibiting the signal. Then the rest is
11:47 kind of a deterministic workflow of if
11:50 it's this company this type of company
11:52 we know that we need to find these types
11:53 of contacts. So then they have the
11:55 enrichment automation and then once you
11:57 have that enrichment automation, put it
11:58 into your sales engagement platform that
12:01 already has either the the pre-built
12:03 messaging in the emails or if you want
12:05 to do um you know manual outreach on top
12:09 of that or it's creating the tasks to
12:11 call these people. Um but that's how I
12:15 do it.
12:15 >> Yeah.
12:16 >> Build out build out a map of everything
12:17 and then build this the pieces for every
12:19 single uh play. So when you're building
12:22 out that map of everything, do you have
12:24 any like guidelines or rules of thumb on
12:26 like the the right level of this is the
12:29 enough detail and then okay now you're
12:31 overdocumenting like it's fine but you
12:33 don't have to waste that much time doing
12:34 it. Like is there a sweet spot that you
12:36 can like recommend on how to people how
12:38 people should like hit that?
12:41 >> Start with one and make sure that you
12:44 get it right. And I I would also start
12:48 with one of your reps who's more tech
12:51 forward, who's already tinkered with
12:53 things on their own or has a has a is
12:56 really bought in
12:58 >> um and just get that one play
13:01 running really smoothly. And I I my my
13:06 guess is if you walk into uh a room with
13:09 all of your reps and you say, "Matt,
13:11 hey, let's what are the best triggers
13:13 that you guys are using that you think
13:15 will work?" You may come up with 20
13:17 ideas, which is great. I I would
13:18 document all of those, but then start
13:21 with the one that's going to be some
13:23 combination of it's a trigger that's
13:25 going to be happening frequently among
13:29 your TAM and
13:32 um it it's one that you've kind of used
13:35 in the past and have a high like you
13:38 have a high degree of confidence that
13:40 messaging is going to resonate
13:41 incrementally more than generic
13:43 messaging.
13:44 >> Yeah. Um and and then the the third
13:47 metric I would consider is easiness to
13:50 build. So ideally it's something that
13:53 you don't have to look at 20 different
13:55 sources in order to to find a signal.
13:58 Start with something that's relatively
14:01 easy to build in terms of it's scanning
14:03 some newsletters. It's looking at one or
14:04 two specific sites. Um so get get that
14:08 done right. build out the the downstream
14:12 plumbing of
14:14 trigger. Find a company, find the people
14:17 to enrich, and move that into a your
14:23 sales engagement platform that you
14:25 already use.
14:26 >> Get the rep to do it for at least a week
14:29 or two. And so you're getting touch
14:31 points and you're generating meetings
14:32 from that. The reality is you're going
14:34 to be able to copy and paste the
14:36 downstream plumbing for most of these
14:39 plays that you're running.
14:40 >> Yeah.
14:41 >> And and then from there, once you have
14:43 one working well, then maybe I would go
14:47 to
14:48 the other reps on your team and say,
14:50 "Hey, here here are all these other
14:52 plays. What have you have you already
14:55 been doing a lot of this stuff on your
14:56 own manually? Would you like to own
14:58 one?" I would almost ask like what what
15:00 do you want to own? and um start diving
15:04 it up that way and and then just
15:06 continue to to build out the the rest of
15:08 these.
15:09 >> Yeah, I like that.
15:10 >> So, oh, sorry, keep going.
15:11 >> Oh, I I was say in terms of amount, I
15:13 don't have a perfect amount of a sweet
15:15 spot of what is the uh the right amount
15:18 to
15:20 to implement on a on a team. I would say
15:22 as many as you can handle. Um, what I
15:25 think you'll probably find is your team
15:27 will quickly come to a conclusion of
15:30 four to five that you know there's
15:31 there's enough happening on a weekly
15:33 basis that these triggers are giving you
15:36 a bunch of leads on a weekly basis. And
15:37 then there's going to be a long tale of,
15:40 you know, this event only happens once a
15:42 month to one person, but when it does,
15:44 we know we want to reach out to them and
15:46 and you'll probably have a dozen or so
15:48 plays like that. But it's good to have
15:49 that going on in the background. But I
15:51 want to be the first one that I build to
15:53 ensure that the whole process is working
15:55 well.
15:56 >> Yeah. I like I was going to say that I
15:57 really like the change management like
15:59 approach that you laid out too. It's
16:00 like find the quick, easy, impactful
16:02 win. Just focus there. Start getting the
16:05 wins. And then if you go into your other
16:06 reps and you're going, well, check out
16:08 all this success over here. when they go
16:11 to look at whether or not they're going
16:12 to want to do it, they're like, "Well, I
16:13 do want all that success, so I guess I
16:15 will kind of do a little extra work that
16:17 I wouldn't ne necessarily do or I'm
16:19 going to buy in when I might have been
16:21 skeptical before." Um, and then, you
16:24 know, I love this thing where you're
16:25 like, "Hey, just take the easy one." And
16:27 then outside of the trigger, once you
16:29 get this thing moving smoothly, and it
16:31 seems like you you get the opportunity
16:32 to refine that on that first go, then
16:36 you can just copy paste it down. Now
16:38 when you copy paste that down would you
16:39 say that there is room for saying okay
16:41 but for this sequence or that this you
16:44 know flow that we have we might make a a
16:47 couple minor adjustments just based on
16:48 things we've noticed even though our
16:50 archetypal approach is always the same
16:52 across or is it like don't mess with
16:54 that because you're going to lose good
16:55 data by switching the different like
16:58 flows that you have set up.
17:00 I think you can tailor it to each
17:02 individual play. And one specific
17:05 example is you. So you might have some
17:09 plays where whenever this happens at a
17:12 company, whenever you see this trigger
17:14 trigger, it it's worth reaching out to,
17:17 you know, five to 10 possible champions
17:20 in a company. And so you want to have
17:22 your enrichment workflow say, "Hey, find
17:25 everybody within this persona or these
17:27 job titles." and then enter them into
17:30 this this downstream s sales engagement
17:33 platform sequence that we've already
17:34 built. But then you might have another
17:37 trigger that it's very specific to an
17:40 individual and so reaching out to 10
17:44 people in the company it's not as
17:45 relevant like you really only want to
17:46 reach out to that one person. So example
17:48 would be like
17:51 >> person change. I think a trigger a lot
17:53 of folks are already using is uh new job
17:56 trigger. And so when you have that you
17:59 you identify somebody, you know, a new
18:01 leader and you want to reach out to
18:02 them. You don't necessarily want to
18:03 reach out to everybody else in in the
18:05 org. So the the that plumbing would be
18:09 oneoff for that specific play, but it
18:12 should be just an easy enough step at
18:15 that piece of of the plumbing. And so
18:18 why I like breaking up the the different
18:21 workflows of the there's the enrichment
18:23 find a company automation, the
18:25 enrichment automation and then the
18:27 pushing it to the sales engagement
18:29 platform automation.
18:31 >> If your enrichment automation changes
18:33 from workflow to workflow, that's just
18:34 one piece that you have to change. You
18:36 don't need to touch these other two
18:37 pieces that are still copy and paste.
18:39 >> Yeah. Nice. Um, so like I love this this
18:43 idea of the trigger, but you know, when
18:45 I'm hearing this, I could see how
18:47 somebody might interpret this is like,
18:48 well, how's that different than a signal
18:49 or how's this different than an
18:51 indicator? How's this different than the
18:52 other ways that people are saying to
18:54 gather information from the market? Uh
18:56 do you have a distinct uh definition
18:58 between like what you mean by trigger
19:00 and then all the other ways that people
19:02 are kind of enriching data for
19:04 prioritization and targeting or would
19:07 you kind of say trigger is the
19:08 overarching version of that?
19:11 >> I'd say it triggers the overarching
19:14 version of that.
19:15 >> Yeah.
19:15 >> Um I I would say
19:22 >> yeah I guess I don't have a great answer
19:24 to that. when when you when you're
19:25 saying between the difference between
19:26 signal and trigger, what were you
19:28 thinking about in your mind? people have
19:30 like, you know, they'll talk about um,
19:32 you know, signals or indicators that
19:34 were like triggers and they'll say
19:35 things like, you know, if somebody like
19:37 a a job posting is like X and then maybe
19:42 like somebody Googled at the
19:44 organization, Y, but then like the
19:47 Google thing is like, well, technically
19:49 it's the IP address and you don't
19:50 actually know who Googled and you can't
19:52 really prove anything with that. But it
19:54 is something that's kind of like letting
19:55 you get a little bit of information from
19:57 the noise versus like something you
19:59 posted a job hiring like that's pretty
20:01 direct in the line. And some people have
20:03 definitions that kind of split those up.
20:05 I was just curious if you had any sort
20:07 of or like no this is like an overall
20:09 thing and then it really is something
20:10 where you can dive into the minutia but
20:12 don't don't separate them I suppose.
20:16 >> Got it. Yeah. I think they they still
20:18 fall into the same
20:19 >> Yeah. um
20:22 strategy of reaching out to people for a
20:24 specific region. Though, yeah, if you're
20:25 using in intentbased signaling at a
20:28 company level with the where the
20:29 upstream data isn't super you don't have
20:32 a ton of confidence in that, then it
20:34 might not be as successful as something
20:35 that's like a very specific trigger or
20:39 uh or signal for a company or individual
20:42 that you saw on the news or based on
20:44 something specific that they did. But I
20:46 think that's an interesting comment that
20:48 that I'll agree with that some some
20:51 triggers or signals are stronger than
20:53 others.
20:54 >> And um and so that's why I recommend
20:57 teams to you know map out all of these
21:00 that you think are going to work. Some
21:02 some will inevitably work stronger than
21:04 than others like the the hiring what
21:07 reference that you just made. Um you
21:09 know just because somebody is hiring
21:11 doesn't mean that they're investing more
21:13 in in their
21:14 >> Yeah. uh their their function overall
21:16 and that it's going to land. Um but it
21:20 means that it could. So with the
21:23 different plays that you have, some will
21:25 certainly be stronger than others, but
21:26 it's good to at least list them all out
21:28 and and and run them all.
21:31 >> What are if I'm sitting here and I'm
21:32 going, "Oh, cool. I really need, you
21:35 know, I I really want to have these
21:36 triggers in here." And besides calling
21:38 you up, Dan, and being like, "Dan, help
21:39 me." like if somebody wanted to get the
21:41 process started themselves or kind of
21:42 kick the tires on it, uh like how would
21:45 you recommend starting with building out
21:47 that list? Like you talked about like
21:48 working through them, but like are there
21:51 like a core three or five that everyone
21:53 should really consider and maybe not
21:55 necessarily use, but at least start
21:57 there and see does this make sense? And
21:59 then once you get to that point, you
22:00 know, how do you brainstorm around ideas
22:03 to you mentioned using SEC filings and
22:06 so like, you know, how do that might be
22:08 something where somebody's like, whoa, I
22:09 would never thought of that, but
22:10 actually, you know what, that actually
22:11 might be helpful. Like what is the
22:13 process around that?
22:15 >> It's going to be unique to whoever
22:19 you're selling to.
22:20 >> Yeah. And so
22:22 what I would do if I was a a sales
22:25 leader in one of these companies that's
22:28 trying to build these out is think
22:31 critically or or talk to
22:34 um I guess your reps, the the marketing
22:37 team around why people buy. Like what's
22:40 what's happening in that organization
22:42 that that means that they're they have a
22:45 higher likelihood of buying. Like I I
22:47 would actually probably talk to the a
22:50 bunch of customers like five to 10
22:52 recent customers around like what what
22:56 made you guys in market for a tool like
22:59 ours and then think through how how can
23:02 you methodically find triggers like
23:05 that. And when it comes to building it
23:08 out, you don't need to you don't
23:11 actually need to vibe code a unique
23:14 clawed agent to build this. A lot of the
23:17 sales engagement platforms, they're
23:18 they're actually investing in um making
23:23 it easier for individual reps even to
23:26 build these intentbased triggers that
23:28 that do all of those steps that I
23:30 mentioned all within the same platform.
23:32 And they'll they'll the first ones that
23:34 that I've seen are ones that a lot of
23:38 folks are already reaching out to. So,
23:40 reaching out after funding
23:42 announcements, after
23:44 new job uh changes, job postings, those
23:49 are probably the the ones that that I
23:50 that I see a lot of. You could ask your
23:52 CEO like what
23:54 >> what uh types of outreach emails are are
23:58 you getting all the time? And that's
23:59 probably the ones that everybody is
24:01 doing. And so there's some value in
24:03 that, but I think what's more valuable
24:05 is this bespoke ones that are unique to
24:07 your persona and
24:10 >> the because that those are the ones that
24:13 your peers probably aren't
24:16 >> um
24:17 >> doing. You're not part of a wave of
24:18 noise when something happens, right?
24:20 you're you're something unique and it
24:22 and it to some degree it makes you
24:24 >> it kind of demonstrates you understand
24:26 their business better because you
24:28 understand better when to reach out to
24:29 them than other folks might or at least
24:32 from a unique perspective because it's
24:34 like you know getting the SEC filings
24:36 and everyone reaches out to you as soon
24:38 as you do your filings which you know
24:39 happened to us I got like a flood of
24:41 like a hundred emails and outreach at
24:43 that exact moment I was like whoa
24:47 >> apparently everyone is aware that we
24:48 just did this and I I didn't even think
24:50 it'd be a blip on the radar. Now,
24:52 obviously, there I'm sure there's
24:53 automation and people weren't actually
24:55 actively paying attention to us, but I
24:57 could see how like something else in our
24:59 business changing and somebody reaches
25:01 out because of a very unique thing that
25:04 they they were monitoring for would make
25:06 them at least stand out just because I
25:08 wouldn't have 100 other emails to be
25:10 kind of overwhelmed by.
25:12 >> Yeah, that's exactly right. um like how
25:15 how can you stand out from the noise and
25:17 getting creative and figuring out what
25:19 are those bespoke signals that that
25:22 aren't necessarily in in the offtheshelf
25:25 um sales engagement platforms but you
25:27 can build either with an AI agent
25:29 builder or yourself with your your own
25:33 claude or or Codex like tool.
25:35 >> Yeah. Yeah. Um, I love your point on the
25:39 um, having like the the voice of the
25:41 customer, the sitting down with your
25:43 customers that you know, the ones that
25:44 like to collaborate with you and be
25:46 like, "Hey, like can you do you mind
25:47 just giving us a little bit more
25:48 information, helping us understand, you
25:50 know, where we could go for that?" Um,
25:53 and from there, is it just like kind of
25:55 sitting down and like having brainstorm
25:57 sessions to figure out, okay, they said
25:59 this, what are some ways that we could
26:01 potentially look at that or like do you
26:02 have any recommendations on how to
26:04 process that information?
26:06 um you know on how to get that that
26:08 great feedback from your customer and
26:09 then turn it into an actual plan.
26:14 >> Yeah,
26:16 it's almost similar to a founder doing
26:21 customer discovery for what is the
26:24 product that that I should buy.
26:26 >> Yeah.
26:26 >> And it it requires just synthesizing a
26:31 number of conversations and finding
26:33 commonalities. Mhm.
26:35 >> Um, so
26:38 I I would just ask the the champion on
26:41 all the the recent deals.
26:44 um like what what made right now
26:48 the right time for you to consider a
26:52 solution like ours?
26:54 >> And um just let them let them chat a
26:58 little bit and you might find that there
27:00 are
27:03 uh my guess is that there'll be just a
27:05 couple reasons of why most of your
27:08 customers buy. It's either the business
27:10 is reaching a certain stage where it's
27:13 having this acute pain now that they
27:15 didn't before or uh or maybe there's
27:19 something else going on in the business.
27:21 It in my experience it's rare that um
27:24 you know a a business is always in
27:27 market for a product all the time. Um,
27:31 and and so I mean maybe they're having
27:33 trouble with like another solution that
27:35 they already had in place, but it's like
27:37 it's just mapping out what were they
27:39 doing before and why did that become
27:42 problematic now versus a year ago and I
27:46 think with enough conversations you
27:47 should be able to have um a handful of
27:50 insights around what was the what was
27:52 the the delta that what was the change
27:55 that happened in the business and then I
27:57 would go a layer deeper around Okay,
28:00 because you had this change in the
28:01 business, how can the outside world
28:03 observe that this is going on or what's
28:06 what's a signal that this is going on? I
28:08 I might ask them. So, I'm just curious
28:10 like when that switch happened like can
28:13 you tell for any of your peers when this
28:15 is also happening and and just hear what
28:16 they
28:18 >> Yeah.
28:18 >> Uh they say and that would be your
28:21 indication that this is a signal that I
28:23 could try to find with the help of AI
28:26 tools.
28:27 >> Yeah. I think you also just made a
28:29 really good um a really good pitch on
28:32 why people need to document their
28:34 discovery calls and actually take good
28:35 notes and get all the information
28:37 because it can turn around and actually
28:38 get them better lead genen if they've
28:40 got that data to then be able to
28:42 leverage back into getting them more
28:44 leads if they get that discovery notes.
28:46 But if you don't capture that
28:47 information, tough luck. You're not
28:49 going to be able to go in and synthesize
28:51 like you're saying. Um well, cool. You
28:53 know, we're at the half hour mark. I
28:55 want to respect your time. Uh but before
28:57 I let you go, I always like to ask
28:59 everybody like if somebody's listening
29:00 in and they were gonna have one
29:02 takeaway, like one thing that they need
29:03 to apply uh to their business after
29:06 listening, like what would that be?
29:13 Send good
29:16 outreach to the right people.
29:18 >> Nice.
29:19 >> As simple as that.
29:20 >> Yeah. uh and AI can help make that more
29:24 efficient, but you you got to be
29:26 effective before you're efficient. And
29:28 so send good outreach and once that
29:31 works, then you can scale it up.
29:33 >> Nice. Appreciate it, Dan. Thank you for
29:35 coming on. Thanks for having me.
Questions answered in this episode
What mistakes do sales teams make with AI lead generation?
Dan highlights buying AI tools without an underlying strategy, spending tokens on tasks that deterministic software already handles, and letting reps build duplicate workflows or target the same accounts without clear ownership.
Where should AI fit in a sales prospecting workflow?
Use AI upstream for research, finding relevant triggers, and prioritizing who to contact and when. Map the downstream data flow and use established automation and sales engagement tools for repeatable tasks and delivery.
How should a team choose its first signal-based prospecting play?
Choose a trigger that appears frequently in the target market, has messaging the team has confidence in, and is relatively easy to find. Start with one willing rep, prove the workflow, and then reuse the downstream steps as other plays are added.
How can customer discovery reveal better prospecting signals?
Talk with recent customers about what changed and why they started looking for a solution. Synthesize common reasons, then ask how those business changes could be observed from outside the company. Use those insights to test more specific outreach triggers.
