Finance Manager

What a great VP Sales does in their first week. Watch for it. One of the most controversial things I've said over the years on SaaStr is: You know within 30 days if you hired a VP right. Especially a VP of Sales. Not at 90 days. Not at 6 months. By day 30, the split is visible. And if you're not paying attention, you'll miss it. Just about every founder and CEO that has been through it agrees with this. A lot of executives challenge it. But it's just as true today in the Age of AI. Maybe even more so. As there just isn't enough time to scale slowly, or hope someone that is scaling slowly... will eventually get there. Great VP of Sales, first week: - brings 2-4 great sales execs in ASAP. often week 1 - identifies top existing talent, does what it takes to keep them - begins to move out underperformers - jumps into all critical deals Mediocre VP of Sales, first month: - has no one to bring... - Jason | SaaStr.Ai | Lemkin (@jasonlk) June 30, 2026 Great VP of Sales: first week. 1. Brings 2-4 great sales execs in ASAP. This is not a maybe. This is not a plan to hire. This is day one through day five. The great VP has already been building their network. They have 3-4 people they've worked with before who know them, who know they can close, and who are ready to move. * Ron Gabrisko joined Databricks as CRO when it was under $1M ARR and immediately brought in salespeople he knew from Cloudera and IBM. His core philosophy: "When you have strong leaders, they bring in their own networks and attract other great talent. That's been a huge part of our early success." Databricks scaled from sub-$1M to over $3B under his leadership. * Matt Plank, who was employee #5 at Rippling, built out the early sales team by focusing on network hires first: "Your first few hires will typically be from your network." He scaled Rippling to over $1B ARR. * Ashley Kelly joined Brex at $2M ARR and immediately brought in three experienced SDRs from her previous company. The network hire is not a nice-to-have. It's the job. If they don't have this network, they are not a great VP. Ever single great sales leader I've ever worked with, and this includes stretch ones, ones that want to be a VP Sales... is cultivating their network. They're constantly making sure the top 2-5 sales execs they know are ready to join their next thing, and they're constantly recruiting one way or another. Constantly. It's the job. Just don't hire anyone for a leadership role that doesn't have a few excellent sales execs to come with them. Trust me. And talk to them (the ones that will join) to confirm it. 2. Identifies top existing talent. Does what it takes to keep them. Week one they're doing 1-on-1s. Not group meetings. Not all-hands listening tours. One on one with everyone, if the team is small. With all your top performers if it's larger. They're asking: What are you doing that works? What's your close rate? What's your deal size? Why are you still here? What would make you leave? The top performers get direct attention from day one. Not later. Not after the process is built. Now. The message is clear: the best people get the best leader's time. Ron Gabrisko's core lesson from scaling Databricks: "Talent beats everything. Culture beats everything. If I could go back, I'd tell myself to invest even more aggressively early on." This means retention conversations with your top reps happen in week one. They make retention offers to these people. Not because it's nice. Because losing your top rep means losing 20-30% of pipeline and breaking morale for everyone else. 3. Begins to move out underperformers. Bad sales reps don't get better. They get slower. They take pipeline from people who can close it. They make the whole team accept mediocrity. The great VP starts this conversation in week one or two. Not cruelly. But fast. "I'm seeing X. Here's what I need to see. If this doesn't change in the next 30 days, we're going to make a change." No second chances. No process that will fix them. No hoping they turn it around. By day 30, 1-2 people are gone or have exit plans. 4. Jumps into all critical deals. Doesn't wait to get "a lay of the land" They spend the first two weeks in deal reviews, and in actual deals. Not strategy sessions. Not CRM reviews. Actual deals. The ones stuck. The ones that should have closed. The ones where something is broken. They're asking: Why is this deal here? Who's the buyer? Have SaaStr Inc. talked to them? What's the objection? Is there a competitive threat? How much revenue is this? Is your rep actually trying? They're not running the deals. They're learning the problems and helping deals close their first week, often their first day. They're seeing which reps know what they're doing and which ones are winging it. They're identifying the patterns. By end of week two, they know what's broken in your sales process. Mediocre VP of Sales: first month. 1. Has no one to bring with them. They show up with no network. No one who will move with them. So they immediately start recruiting, which means they're building a plan instead of executing. They spend weeks 1-2 writing a hiring plan. A sales process. A CRM framework. A training program. They're trying to fix what's broken through systems instead of people. If this is your VP, you've already made the hire wrong. 2. Top talent begins to leave. Your A player is watching. They see that the new VP doesn't know anyone. Doesn't have gravity. Is focused on meetings instead of deals. They get a call from a recruiter on Wednesday and take a coffee on Friday. Your top revenue driver sees a founder at a competitor who moves faster. By week two, she's seriously looking. Your third-best person hasn't heard from the new VP at all. They're wondering if they matter anymore. By day 21, you've lost one person or are about to. If you ask them why, they say "I'm just looking for something new" or "The opportunity came up." What they're actually saying is: I don't trust this hire. 3. Tries hard to keep everyone, including low performers. The mediocre VP focuses on retention because that's what you asked for. "Jason left, we need to keep people happy." So they build retention plans. They promise more coaching. Better commission plans. More training. They try to make the process so good that people don't leave. But they're not fixing the real problem: underperformers are still here. Pipeline is still stuck. They're still building process instead of executing. So people who could win somewhere else stay just long enough to see that nothing is changing, then leave anyway. And people who are costing you money stay forever because there's no accountability. By day 30, your team is the same size but demoralized. Your bad performers have permission to stay. Your good performers are checking out. 4. Works mainly on process. Week 1: Sales process documentation. Week 2: CRM cleanup and reporting. Week 3: New comp plan proposal. Week 4: Training schedule. Nothing about this is wrong. It's just not the job of a VP of Sales in their first month. The job is: fix what's actually broken, move the right people into place, and get the organization moving. Process is the thing you build after your team actually believes in you. Process without trust is just meetings. What you'll actually see. By day 30, if you're paying attention: Great VP scenario: * 2-3 new people in the door * 2-3 underperformers either gone or have 30-day exit plans * Your top performers have had real conversations about why they're staying * 1-2 critical deals have moved or are close to moving * Your sales team believes this person knows what they're doing Mediocre VP scenario: * No new people hired yet, but lots of job reqs posted * Your top person either left or is actively looking * Everyone is still here, including the people who can't close * You have a new sales process doc and a meeting schedule * Your sales team is wondering who this person is and what they're trying to do The great VP can even make you uncomfortable. They move fast. They make hard decisions. They do things without consensus. They are confident by the end of Week 1 at least in 2-3 things that truly will move the needle, and they can tell you exactly why., The mediocre VP makes you feel heard. They listen. They build lots and lots of plans. They're professional. They often are pretty darn good at selling up. They do a lot of listening tours to start. Your board and investors may even love them. By month two, you'll know which one you hired. You'll even know at the end of Week 1 if you really listen and watch. The hard part is: most founders hire the mediocre one because they seem competent in the interview, and often have the best LinkedIn. The great one often seems reckless.

Flex raises $70 million to improve payments for high net worth business owners. * Business banking platform Flex raised $70 million in a Series B1 round to expand its business finance, payments, private credit, and ERP offerings while doubling its workforce. * The company also launched Flex Global, a cross-border banking service that combines multi-currency accounts, global payments, and stablecoin infrastructure to enable faster international money movement. * With Flex Global, Flex is positioning itself to compete more directly with Brex and Ramp by offering globally active businesses a unified platform that blends banking, payments, credit, and wealth management. The business banking space is heating up again. Business banking platform Flex landed $70 million in a Series B1 investment, boosting its total equity funding to $180 million and total debt funding to $300 million. Halo Fund lead the investment, which comes seven months after Flex's $60 million Series B round. Portage Ventures, Wellington, Crosslink Capital, 53 Stations, Titanium Ventures, Spice, Florida Funders, Spice, and others also contributed. Halo's participation is especially notable, as its co-founders span the sports and entertainment space, bringing expertise in sports and entertainment distribution into audiences that include millions of successful middle-market business owners and entrepreneurs. With this round, Flex plans to expand across business finance, personal finance, payments, private credit, and ERP. The company will also use the funds to double the team size from 110 employees to more than 200 by year-end. Flex made its debut in 2022 to bring private banking to high net worth business owners. The California-based company offers banking, private credit, payments, billing, and accounting tools for businesses, as well as a business credit card that pays up to 5% cashback. The company's average customer uses four or more of these products on its platform. Flex has crossed $10 billion in annualized total payment volume and is currently growing 4x year-over-year. "I've spent my career helping entrepreneurs win, and they all have the same problem: their business and personal financial lives are completely intertwined, but every bank treats them as two different customers, missing what they're actually trying to build," said Halo Fund Owner Co-founder Ryan Smith. "Flex is the first team creating a real private bank around the owner and the entire household's finances, and the gap they're filling is just as real globally as it is in the US. Zaid and the team have built an enduring business that is becoming an institution for the world's most ambitious owners." Along with today's funding announcement, Flex is launching Flex Global, a service that brings together local currency accounts, cross-border payments, and stablecoins for always-on, fast funds transfers. The service is aimed to serve cross-border businesses by issuing global credit cards, leveraging stablecoin payment rails and wallets in 100+ countries, and offering institutional USD accounts for foreign business owners. Flex's multi-currency accounts support 32 currencies across 76 countries, enabling busineses to hold, send, and receive funds in the currencies they actually operate in. Flex's goal is to make the underlying payment rails invisible to customers by embedding stablecoin settlement into its private banking experience. Rather than requiring businesses to manage crypto wallets or navigate blockchain technology, Flex uses stablecoins behind the scenes to make international payments feel as seamless as domestic ones. "Middle-market business owners are one of the most important and underserved customers in finance globally," said Flex CEO and Founder Zaid Rahman. "Depending on the type of owner, they'll tell you their vendors are spread across the US, Poland, Brazil, etc; their accounts hold currency outside of just USD; and they have to oscillate across 2-3 vendors and layers of fees just to do business outside their country." Flex Global raises the competitive stakes for Brex and Ramp by expanding Flex beyond domestic banking, credit, and expense management into global financial infrastructure. Both rivals already support international cards and vendor payments, while Brex has also been developing stablecoin-based global transfers. Flex differentiates itself with its focus on middle-market business owners and its effort to combine cross-border payments, multi-currency accounts, credit, banking, and personal wealth management within a single private-banking relationship. That approach could help Flex compete less as another spend-management platform and more as the primary financial institution for globally active entrepreneurs.