From In-House Headaches to AI Insights: Poppy’s Quest to Shape the Future of Spend Management
When you ask attorney-turned-entrepreneur Jesse Soslow why he started Poppy Legal, a pattern emerges: his insights come from problems he’s personally experienced. As a former general counsel at multiple tech startups, including Everwise and the blockchain pioneer Blockstack (now Hiro), Soslow spent years juggling contracts, compliance checklists, and ballooning outside counsel bills. But it wasn’t the complexity alone that got to him. “One company in particular…we did the first ever SEC-qualified [offering] of a digital asset,” he says, referencing Blockstack’s 2019 landmark token sale. “There was a ton of legal expense involved…and when you looked out at the landscape of what could I use to make sure we’re staying on track, there wasn’t much for a team our size.”
His frustrations with legal billing were far from niche. At smaller startups, budgets are tight, bandwidth is limited, and the average GC or one-person legal operations department quickly becomes the de facto administrator for all sorts of finance and operational tasks. He recalled instances of missing negotiated discounts because of the difficulties of tracking them by hand. “It took me three or four months to realize…it wasn’t being applied,” he says. That memory lapse inspired him to launch Poppy Legal, a spend-management tool that aims to simplify life for legal teams, especially the ones that, as Soslow puts it, don’t want to “have headcount to manage it.”
“We want this to be just as useful for a solo GC as it is for a 10-, 20-, 30-person legal team”
Rather than layering the platform with complex integrations, Poppy seeks to create a “super easy to implement and super easy to manage” experience. “We want this to be just as useful for a solo GC as it is for a 10-, 20-, 30-person legal team,” Soslow explains. Drawing on years in operations and finance, he zeroed in on the challenge that legal departments often don’t know where money is going, sometimes literally. “With multiple customers we have seen bills come in where the line items don't add up to the invoice total,” he notes. Predictably, he says, “The total amount has been larger [than it should have been].”
No wonder larger corporations have also shown interest in Poppy’s platform, even if the original target was small legal departments. “We’ve found some interest from larger teams…that we hadn’t contemplated initially,” he observes. After all, the trend toward doing more with less is hardly limited to startups. With mounting economic pressures, in-house legal teams - big or small - are rethinking staffing, outside counsel relationships, and what artificial intelligence might accomplish. “You can’t have this conversation without discussing AI,” he says. “For lawyers, it puts them in a tricky spot…we have an obligation to make sure things are right, and sometimes that negates efficiency gains a little bit. But…there is certainly a perception, particularly from non-lawyers, that AI can do a lot of the work they’re doing.”
“We provide insights that will be helpful to teams as they negotiate their rates or their discount for the following year”
Soslow’s perspective on AI feels balanced: part excitement, part caution. He’s seen hype cycles come and go. During his days in crypto, he witnessed plenty of “untethered optimism,” and he expects AI to enjoy its own boom (and possible bust) before settling into proven usefulness. That’s why Poppy employs AI “in a way that is realistic with its current capabilities,” focusing on consistent data review rather than more speculative - and inherently risky - use cases. The platform flags invoice anomalies, helps track negotiated rates, and provides year-over-year insights about a law firm’s billing patterns. “We provide insights that will be helpful to teams as they negotiate their rates or their discount for the following year,” he says.
Part of Soslow’s confidence in building Poppy comes from his cross-functional background. He has long worn multiple hats - legal, finance, HR, operations - and encourages others to learn enough “to speak the language of tech.” What advice would he give legal professionals who find themselves needing to work across departments? “For me, it’s always been driven by genuine interest.” Curiosity, it seems, is the key to translating between different disciplines.
Looking ahead, Soslow predicts a shift toward fewer attorneys and more “operator”-focused professionals, in-house or otherwise, especially as AI-driven workflows gain traction. Yet he believes in-house teams will need better oversight of their outside counsel too. “Am I being billed for a bunch of stuff that could very well be done by an AI tool?” he asks, voicing the concern many legal departments may soon share.
If you ask him about Poppy’s future, he’ll say he’s aiming for a blend of short-term invoice audits and longer-term billing and relationship insights. “We have a ton of features in the pipeline…Poppy’s ability to analyze a law firm relationship holistically” is high on his list, leveraging AI across an entire year of billables rather than on an invoice-by-invoice basis. In doing so, Soslow hopes to offer a platform that suits scrappy startups, risk-averse enterprise legal teams, and the vast array of businesses in between (from traditional industries to fast-growing innovators) so that no one is left fuming over missed discounts or miscalculated bills.
For Soslow, that might be the greatest triumph: turning a legacy headache into a seamless, data-rich experience. And if he can help legal teams save money along the way? So much the better.
When you ask attorney-turned-entrepreneur Jesse Soslow why he started Poppy Legal, a pattern emerges: his insights come from problems he’s personally experienced. As a former general counsel at multiple tech startups, including Everwise and the blockchain pioneer Blockstack (now Hiro), Soslow spent years juggling contracts, compliance checklists, and ballooning outside counsel bills. But it wasn’t the complexity alone that got to him. “One company in particular…we did the first ever SEC-qualified [offering] of a digital asset,” he says, referencing Blockstack’s 2019 landmark token sale. “There was a ton of legal expense involved…and when you looked out at the landscape of what could I use to make sure we’re staying on track, there wasn’t much for a team our size.”
His frustrations with legal billing were far from niche. At smaller startups, budgets are tight, bandwidth is limited, and the average GC or one-person legal operations department quickly becomes the de facto administrator for all sorts of finance and operational tasks. He recalled instances of missing negotiated discounts because of the difficulties of tracking them by hand. “It took me three or four months to realize…it wasn’t being applied,” he says. That memory lapse inspired him to launch Poppy Legal, a spend-management tool that aims to simplify life for legal teams, especially the ones that, as Soslow puts it, don’t want to “have headcount to manage it.”
“We want this to be just as useful for a solo GC as it is for a 10-, 20-, 30-person legal team”
Rather than layering the platform with complex integrations, Poppy seeks to create a “super easy to implement and super easy to manage” experience. “We want this to be just as useful for a solo GC as it is for a 10-, 20-, 30-person legal team,” Soslow explains. Drawing on years in operations and finance, he zeroed in on the challenge that legal departments often don’t know where money is going, sometimes literally. “With multiple customers we have seen bills come in where the line items don't add up to the invoice total,” he notes. Predictably, he says, “The total amount has been larger [than it should have been].”
No wonder larger corporations have also shown interest in Poppy’s platform, even if the original target was small legal departments. “We’ve found some interest from larger teams…that we hadn’t contemplated initially,” he observes. After all, the trend toward doing more with less is hardly limited to startups. With mounting economic pressures, in-house legal teams - big or small - are rethinking staffing, outside counsel relationships, and what artificial intelligence might accomplish. “You can’t have this conversation without discussing AI,” he says. “For lawyers, it puts them in a tricky spot…we have an obligation to make sure things are right, and sometimes that negates efficiency gains a little bit. But…there is certainly a perception, particularly from non-lawyers, that AI can do a lot of the work they’re doing.”
“We provide insights that will be helpful to teams as they negotiate their rates or their discount for the following year”
Soslow’s perspective on AI feels balanced: part excitement, part caution. He’s seen hype cycles come and go. During his days in crypto, he witnessed plenty of “untethered optimism,” and he expects AI to enjoy its own boom (and possible bust) before settling into proven usefulness. That’s why Poppy employs AI “in a way that is realistic with its current capabilities,” focusing on consistent data review rather than more speculative - and inherently risky - use cases. The platform flags invoice anomalies, helps track negotiated rates, and provides year-over-year insights about a law firm’s billing patterns. “We provide insights that will be helpful to teams as they negotiate their rates or their discount for the following year,” he says.
Part of Soslow’s confidence in building Poppy comes from his cross-functional background. He has long worn multiple hats - legal, finance, HR, operations - and encourages others to learn enough “to speak the language of tech.” What advice would he give legal professionals who find themselves needing to work across departments? “For me, it’s always been driven by genuine interest.” Curiosity, it seems, is the key to translating between different disciplines.
Looking ahead, Soslow predicts a shift toward fewer attorneys and more “operator”-focused professionals, in-house or otherwise, especially as AI-driven workflows gain traction. Yet he believes in-house teams will need better oversight of their outside counsel too. “Am I being billed for a bunch of stuff that could very well be done by an AI tool?” he asks, voicing the concern many legal departments may soon share.
If you ask him about Poppy’s future, he’ll say he’s aiming for a blend of short-term invoice audits and longer-term billing and relationship insights. “We have a ton of features in the pipeline…Poppy’s ability to analyze a law firm relationship holistically” is high on his list, leveraging AI across an entire year of billables rather than on an invoice-by-invoice basis. In doing so, Soslow hopes to offer a platform that suits scrappy startups, risk-averse enterprise legal teams, and the vast array of businesses in between (from traditional industries to fast-growing innovators) so that no one is left fuming over missed discounts or miscalculated bills.
For Soslow, that might be the greatest triumph: turning a legacy headache into a seamless, data-rich experience. And if he can help legal teams save money along the way? So much the better.
