StarZero All shows Try the podcast clipper →

Oct 21, 2021 · 16m · top-founders

SalesChoice Bootstrapped to $1m in ARR on Salesforce, Now Raising $2-3m

Dr. Cindy Gordon · 9m spoken Nathan Latka · 4m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

SalesChoice founder and CEO Dr. Cindy Gordon discusses how she bootstrapped her predictive AI sales analytics platform to over $1 million in ARR and outlines her plans to raise a $2 to $3 million institutional round to scale enterprise growth.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 32.6% of the talking time here. How this is scored →

Nathan as informed peer 4.8 Guest teaching 3.0 Guest disagreement 4.0 Nathan pushing back 5.0
05100:0010:000:45–5:11 · Nathan as informed peer 6/10 Introducing Dr. Cindy Gordon and SalesChoice Nathan drills into the unit economics and channel risk with Salesforce, trying to pin down whether Gordon's $100k ACV is an aspirational goal or an existing average. Gordon clarifies that they are purely an enterprise play averaging well above small monthly figures and pushes back on the risk of being booted from AppExchange.5:11–8:52 · Nathan as informed peer 5/10 Founding Timeline, Patents, and Team Size Gordon explicitly refuses to disclose engineering headcounts, prompting Nathan to playfully challenge her by threatening to pause and look up the data live on Owler/LinkedIn. Gordon relents slightly by sharing an overall company size of around 20 employees.8:52–10:54 · Nathan as informed peer 5/10 Enterprise Clients and Target Industry Verticals Gordon refuses to state her customer count citing privacy, so Nathan works around her guardrails by reading off the case study logos directly from her website to establish a baseline of at least 10 enterprise clients. Gordon agrees and explains their focus on logistics and tech verticals.10:54–13:15 · Nathan as informed peer 5/10 Fundraising Strategy and Enterprise Sales Talent The exchange becomes collaborative as Gordon shares insights from her VC background regarding fundraising targets ($2-3M) and the difficulty of building repeatable enterprise sales capacity. Nathan probes into quota attainment and sales motion repeatability.13:15–15:40 · Nathan as informed peer 3/10 The Famous Five Rapid-Fire Questions During the rapid-fire section, Gordon flatly refuses to answer Nathan's question about her age. Nathan politely respects the boundary and moves on to the final reflection question.0:45–5:11 · Guest teaching 4/10 Introducing Dr. Cindy Gordon and SalesChoice Nathan drills into the unit economics and channel risk with Salesforce, trying to pin down whether Gordon's $100k ACV is an aspirational goal or an existing average. Gordon clarifies that they are purely an enterprise play averaging well above small monthly figures and pushes back on the risk of being booted from AppExchange.5:11–8:52 · Guest teaching 3/10 Founding Timeline, Patents, and Team Size Gordon explicitly refuses to disclose engineering headcounts, prompting Nathan to playfully challenge her by threatening to pause and look up the data live on Owler/LinkedIn. Gordon relents slightly by sharing an overall company size of around 20 employees.8:52–10:54 · Guest teaching 2/10 Enterprise Clients and Target Industry Verticals Gordon refuses to state her customer count citing privacy, so Nathan works around her guardrails by reading off the case study logos directly from her website to establish a baseline of at least 10 enterprise clients. Gordon agrees and explains their focus on logistics and tech verticals.10:54–13:15 · Guest teaching 4/10 Fundraising Strategy and Enterprise Sales Talent The exchange becomes collaborative as Gordon shares insights from her VC background regarding fundraising targets ($2-3M) and the difficulty of building repeatable enterprise sales capacity. Nathan probes into quota attainment and sales motion repeatability.13:15–15:40 · Guest teaching 2/10 The Famous Five Rapid-Fire Questions During the rapid-fire section, Gordon flatly refuses to answer Nathan's question about her age. Nathan politely respects the boundary and moves on to the final reflection question.0:45–5:11 · Guest disagreement 3/10 Introducing Dr. Cindy Gordon and SalesChoice Nathan drills into the unit economics and channel risk with Salesforce, trying to pin down whether Gordon's $100k ACV is an aspirational goal or an existing average. Gordon clarifies that they are purely an enterprise play averaging well above small monthly figures and pushes back on the risk of being booted from AppExchange.5:11–8:52 · Guest disagreement 6/10 Founding Timeline, Patents, and Team Size Gordon explicitly refuses to disclose engineering headcounts, prompting Nathan to playfully challenge her by threatening to pause and look up the data live on Owler/LinkedIn. Gordon relents slightly by sharing an overall company size of around 20 employees.8:52–10:54 · Guest disagreement 5/10 Enterprise Clients and Target Industry Verticals Gordon refuses to state her customer count citing privacy, so Nathan works around her guardrails by reading off the case study logos directly from her website to establish a baseline of at least 10 enterprise clients. Gordon agrees and explains their focus on logistics and tech verticals.10:54–13:15 · Guest disagreement 2/10 Fundraising Strategy and Enterprise Sales Talent The exchange becomes collaborative as Gordon shares insights from her VC background regarding fundraising targets ($2-3M) and the difficulty of building repeatable enterprise sales capacity. Nathan probes into quota attainment and sales motion repeatability.13:15–15:40 · Guest disagreement 4/10 The Famous Five Rapid-Fire Questions During the rapid-fire section, Gordon flatly refuses to answer Nathan's question about her age. Nathan politely respects the boundary and moves on to the final reflection question.0:45–5:11 · Nathan pushing back 5/10 Introducing Dr. Cindy Gordon and SalesChoice Nathan drills into the unit economics and channel risk with Salesforce, trying to pin down whether Gordon's $100k ACV is an aspirational goal or an existing average. Gordon clarifies that they are purely an enterprise play averaging well above small monthly figures and pushes back on the risk of being booted from AppExchange.5:11–8:52 · Nathan pushing back 7/10 Founding Timeline, Patents, and Team Size Gordon explicitly refuses to disclose engineering headcounts, prompting Nathan to playfully challenge her by threatening to pause and look up the data live on Owler/LinkedIn. Gordon relents slightly by sharing an overall company size of around 20 employees.8:52–10:54 · Nathan pushing back 6/10 Enterprise Clients and Target Industry Verticals Gordon refuses to state her customer count citing privacy, so Nathan works around her guardrails by reading off the case study logos directly from her website to establish a baseline of at least 10 enterprise clients. Gordon agrees and explains their focus on logistics and tech verticals.10:54–13:15 · Nathan pushing back 4/10 Fundraising Strategy and Enterprise Sales Talent The exchange becomes collaborative as Gordon shares insights from her VC background regarding fundraising targets ($2-3M) and the difficulty of building repeatable enterprise sales capacity. Nathan probes into quota attainment and sales motion repeatability.13:15–15:40 · Nathan pushing back 3/10 The Famous Five Rapid-Fire Questions During the rapid-fire section, Gordon flatly refuses to answer Nathan's question about her age. Nathan politely respects the boundary and moves on to the final reflection question.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 53.6% · guest 46.4%0:00 · Nathan 53.6% · guest 46.4%3:00 · Nathan 23.1% · guest 76.9%3:00 · Nathan 23.1% · guest 76.9%6:00 · Nathan 29.8% · guest 70.2%6:00 · Nathan 29.8% · guest 70.2%9:00 · Nathan 26.9% · guest 73.1%9:00 · Nathan 26.9% · guest 73.1%12:00 · Nathan 23.5% · guest 76.5%12:00 · Nathan 23.5% · guest 76.5%15:00 · Nathan 47.7% · guest 52.3%15:00 · Nathan 47.7% · guest 52.3%
Sharpest disagreement ▶ 6:05 Refusal to disclose team size and private data

Gordon pushes back against Nathan's probing on engineering team numbers, telling him to look it up on Owler because she will not reveal private company details.

 Hardest push from Nathan ▶ 6:30 Nathan pulls up public records live on air

Nathan rejects Gordon's dodge about team size and forces the issue by pulling up LinkedIn and Owler in real time until she concedes an overall headcount.

 Biggest teaching moment ▶ 12:24 Gordon explains the complexity of selling enterprise AI

Gordon educates Nathan on why standard BDR motions fail in deep enterprise AI sales, requiring high-caliber MBAs and engineering backgrounds to interface with CROs.

 Nathan holds their own ▶ 9:28 Nathan calculates client floor using public website logos

When Gordon declines to share customer counts, Nathan reads back every client logo listed on her live website to establish firm ground metrics without her direct disclosure.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing Dr. Cindy Gordon and SalesChoice 6435 Nathan drills into the unit economics and channel risk with Salesforce, trying to pin down whether Gordon's $100k ACV is an aspirational goal or an existing average. Gordon clarifies that they are purely an enterprise play averaging well above small monthly figures and pushes back on the risk of being booted from AppExchange.
Founding Timeline, Patents, and Team Size 5367 Gordon explicitly refuses to disclose engineering headcounts, prompting Nathan to playfully challenge her by threatening to pause and look up the data live on Owler/LinkedIn. Gordon relents slightly by sharing an overall company size of around 20 employees.
Enterprise Clients and Target Industry Verticals 5256 Gordon refuses to state her customer count citing privacy, so Nathan works around her guardrails by reading off the case study logos directly from her website to establish a baseline of at least 10 enterprise clients. Gordon agrees and explains their focus on logistics and tech verticals.
Fundraising Strategy and Enterprise Sales Talent 5424 The exchange becomes collaborative as Gordon shares insights from her VC background regarding fundraising targets ($2-3M) and the difficulty of building repeatable enterprise sales capacity. Nathan probes into quota attainment and sales motion repeatability.
The Famous Five Rapid-Fire Questions 3243 During the rapid-fire section, Gordon flatly refuses to answer Nathan's question about her age. Nathan politely respects the boundary and moves on to the final reflection question.

Statements from this episode (12)

Disclosure
Gordon: SalesChoice is only integrated with Salesforce AppExchange
“We're only integrated with the app exchange at this point, although we have an open API.”
Dr. Cindy Gordon Oct 21, 2021 ▶ 1:40
Opinion
Gordon: Salesforce rarely boots partner apps from AppExchange after acquisitions
“I don't know if that happens too often. I think within the ecosystem I mean, I'd love to hear your perspective, but I haven't heard those stories.”
Dr. Cindy Gordon Oct 21, 2021 ▶ 1:56
Disclosure
Gordon: SalesChoice base pricing is $50 CAD per seat per month
“We're priced at 50 dollars Canadian.”
Dr. Cindy Gordon Oct 21, 2021 ▶ 2:34
Assertion Not checkable as stated
Gordon: SalesChoice client revenue averages well above $4,000 monthly
“No, no. We basically are averaging a much higher ratio than four K a month on our clients.”
Dr. Cindy Gordon Oct 21, 2021 ▶ 4:32
Opinion
Gordon: SalesChoice only works for mid-market and large enterprise
“First of all, are the kind of use case that we have, it only will really work well with mid upper mid market and large enterprise. So we're not a small business play at all.”
Dr. Cindy Gordon Oct 21, 2021 ▶ 4:56
Assertion Not checkable as stated
Gordon: SalesChoice has a total team size of about 20
“We're all up. We're probably about 20 here.”
Dr. Cindy Gordon Oct 21, 2021 ▶ 6:53
Insight
Gordon: Salespeople have zero patience for low-quality AI agents
“It's so easy to surface crap with these AI agents and not, and salespeople have zero, they have zero patients. If you're not delivering value from the get go, you know, it won't last.”
Dr. Cindy Gordon Oct 21, 2021 ▶ 8:40
Assertion Not checkable as stated
Gordon: Purolator is SalesChoice's largest client account
“Purelator would be, it's a two billion dollar company. So that's one of our largest accounts where we're, you know, running all of their insights for, you know, all channels in the company.”
Dr. Cindy Gordon Oct 21, 2021 ▶ 9:19
Disclosure
Gordon: SalesChoice is doubling down on transportation and tech verticals
“I think we've decided we're going to really double down hard on just two industries. I think we've maybe gone a little bit too broad. I think the two that are the most promising are probably the transportation logistics and probably the broad technology sector…”
Dr. Cindy Gordon Oct 21, 2021 ▶ 10:09
Disclosure
Gordon: SalesChoice is targeting a $2M to $3M fundraise
“I think probably a raise between two to three million is probably a good target. You know, typically you can't get a Firm in unless you're raising at least a million, right? So we've kind of got an overall goal. We don't need a lot of capital. I just want to b…”
Dr. Cindy Gordon Oct 21, 2021 ▶ 11:39
Disclosure
Gordon: SalesChoice has not yet reached a repeatable sales quota model
“We actually have a few people in sales now. I don't think that it's in that repeatable zone. I think that's the one that we're still figuring out hard, right?”
Dr. Cindy Gordon Oct 21, 2021 ▶ 12:25
Insight
Gordon: Enterprise AI sales requires engineering or MBA talent, not traditional BDRs
“We've learned that because to sell AI and advanced analytics, you have to hire probably an engineering base. And also an MBA is, is not a bad idea because the kinds of people that we like to hit, we don't sell low, right? So these decisions usually have to be …”
Dr. Cindy Gordon Oct 21, 2021 ▶ 12:46
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 2,600 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more