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    John DiFucciGuggenheim Securities

    John DiFucci's questions to OneStream Inc (OS) leadership

    John DiFucci's questions to OneStream Inc (OS) leadership • Q2 2025

    Question

    John DiFucci asked about OneStream's go-to-market strategy for operational planning beyond the CFO's office and questioned the visibility behind the Q3 guidance concerning the US federal sector.

    Answer

    CEO & President Tom Shea explained the strategy centers on productizing targeted use cases, like ESG, built on the core platform's Agile Financial Analytics (AFA) capabilities. CFO Bill Koefoed added that the Q3 guidance balances near-term prudence regarding federal spending with the strongest second-half pipeline in the company's history, noting the government's long-term push to modernize and adopt SaaS.

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    John DiFucci's questions to OneStream Inc (OS) leadership • Q1 2025

    Question

    John DiFucci of Guggenheim Securities questioned why OneStream did not raise its full-year guidance despite a strong Q1, asking if the unchanged outlook was due to prudence or an observed slowdown in demand.

    Answer

    CFO Bill Koefoed explained that while leading indicators like the sales pipeline are the strongest they have ever been, the company is remaining prudent and cautious due to heightened macroeconomic uncertainty. He clarified that they have not yet seen a slowdown in their current results.

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    John DiFucci's questions to OneStream Inc (OS) leadership • Q4 2024

    Question

    John DiFucci of Guggenheim Securities inquired about the drivers behind the improving demand for modern consolidation and planning solutions, noting it seems to be a higher priority than other back-office applications.

    Answer

    Co-Founder and CEO Tom Shea explained that OneStream's core solution is essential for every finance team, and companies recognize they can no longer delay modernizing these critical systems. He emphasized that the company's 98% gross retention rate creates a durable customer base, which serves as a foundation for upselling new solutions like their finance AI portfolio. Shea added that the vast amount of curated financial data OneStream holds for customers is a significant asset for powering future AI-driven applications.

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    John DiFucci's questions to OneStream Inc (OS) leadership • Q3 2024

    Question

    John DiFucci of Guggenheim Securities noted the market's focus on OneStream's consolidation/close replacement success and asked about the traction seen in financial and operational planning, independent of the close process.

    Answer

    CEO Tom Shea expressed excitement for the question, confirming significant traction in planning. He explained that OneStream's strategy is to first make core finance processes (like consolidation) efficient. This allows customers to then leverage the platform for more strategic activities, linking operational plans to financial objectives to holistically manage and drive the business forward.

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    John DiFucci's questions to Progress Software Corp (PRGS) leadership

    John DiFucci's questions to Progress Software Corp (PRGS) leadership • Q2 2025

    Question

    John DiFucci of Guggenheim Securities inquired if the Nuclea acquisition could be leveraged across Progress's entire product portfolio, unlike typical standalone acquisitions. He also asked for clarification on the quarterly free cash flow performance versus the raised annual forecast.

    Answer

    CEO Yogesh Gupta confirmed Nuclea is designed for integration across the entire portfolio, including the data platform, Sitefinity, and ShareFile. Regarding cash flow, CFO Anthony Folger attributed the quarterly result to collection timing and the deliberate, careful process of migrating the entire ShareFile business onto Progress's billing system, which was a major integration milestone.

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    John DiFucci's questions to Progress Software Corp (PRGS) leadership • Q1 2025

    Question

    On behalf of John DiFucci from Guggenheim Securities, Lauren Sanco asked if Progress has seen any business changes in major international geographies due to geopolitical forces.

    Answer

    CEO Yogesh Gupta responded that they have not seen any resulting changes, either positive or negative, in their international business. He attributed the stability to the company's products being deeply embedded in customers' mission-critical operations and the long-term trust built with their global customer base.

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    John DiFucci's questions to Progress Software Corp (PRGS) leadership • Q4 2024

    Question

    John DiFucci asked how higher interest rates and the political administration might impact Progress's M&A strategy. He also asked if the company would begin to break out SaaS revenue, given that ShareFile will make it nearly 30% of the total.

    Answer

    CEO Yogesh Gupta stated there would be 'no pause' to the M&A strategy, arguing that higher interest rates create a competitive advantage and lead to more reasonable valuations. EVP & CFO Anthony Folger confirmed it is 'likely' that Progress will introduce a 'services' line in its P&L during 2025, which will primarily consist of SaaS solutions, to provide better modeling clarity for investors.

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    John DiFucci's questions to Progress Software Corp (PRGS) leadership • Q3 2024

    Question

    John DiFucci asked for clarification on the free cash flow guidance, noting an implied raise excluding the ShareFile acquisition. He also questioned Progress's confidence in elevating ShareFile's profit and cash flow metrics to its own standards, given the deal's size, and inquired about potential weakness in the SMB market, a key customer base for ShareFile.

    Answer

    CFO Anthony Folger confirmed the implied increase in the core business's free cash flow guidance. He detailed the confidence in integrating ShareFile, citing its existing profitability, scalable cloud platform, strong gross margins, and the favorable structure of the carve-out. CEO Yogesh Gupta added that ShareFile's customer base is stable due to its mission-critical nature in regulated industries and that non-linear R&D scaling provides a clear path to the 40% operating margin target.

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    John DiFucci's questions to Oracle Corp (ORCL) leadership

    John DiFucci's questions to Oracle Corp (ORCL) leadership • Q4 2025

    Question

    John DiFucci from Guggenheim Partners questioned the drivers behind the strong forward guidance, asking if the 'Stargate' project is a key component of the forecasted 70%+ IaaS and 100%+ RPO growth.

    Answer

    CEO Safra Catz stated that while the Stargate project is still in formation, related partnerships contribute to the outlook, which is primarily driven by massive, broad-based demand for AI and database workloads that currently outstrips supply. CTO Larry Ellison added that other large contracts, like one with TIMU, and rapid multi-cloud growth are also significant contributors, noting that the RPO forecast would be an understatement if Stargate meets expectations.

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    John DiFucci's questions to Oracle Corp (ORCL) leadership • Q3 2025

    Question

    John DiFucci of Guggenheim Securities questioned the deployment timeline for the 40 planned multi-cloud regions with partners like Azure, AWS, and Google, noting that a lack of global footprint may be delaying deal closures for large enterprises.

    Answer

    CEO Safra Catz explained that hyperscaler partners are highly motivated to deploy these regions quickly to unlock revenue, with competition among them accelerating the process. Executive Chairman and CTO Lawrence Ellison added that achieving a global footprint (primary/backup in North America, Europe, Asia) is the key milestone, and he expects to meet most multinational customer needs within the coming months, estimating the full 40 regions could be deployed in about 12 months.

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    John DiFucci's questions to Oracle Corp (ORCL) leadership • Q2 2025

    Question

    John DiFucci requested an update on the progress of OCI gross margins, noting past commentary about consistent improvement and questioning how they are trending given the massive growth.

    Answer

    CEO Safra Catz affirmed that OCI gross margins are continuing to improve, even with heavy investment and the growth of GPU business. She attributed the trend to the architectural advantages and high degree of automation that Larry Ellison described, which create significant operating leverage. Catz stated that both OCI and SaaS margins are improving with scale.

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    John DiFucci's questions to Oracle Corp (ORCL) leadership • Q1 2025

    Question

    John DiFucci of Guggenheim Securities asked how Oracle's overall margins and profitability will be affected by the continued mix shift towards the lower-margin OCI business, despite its rapid growth.

    Answer

    CEO Safra Catz stated that OCI's gross margins are increasing with scale, partly because OCI includes high-margin services like the expanding Autonomous Database. Chairman and CTO Larry Ellison added that moving applications like Fusion to the Autonomous Database provides huge cost savings (estimated around 50%) and stunningly high margins due to automation eliminating human labor and improving hardware efficiency. He affirmed his belief that both profit dollars and profit margins will increase over time.

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    John DiFucci's questions to Rubrik Inc (RBRK) leadership

    John DiFucci's questions to Rubrik Inc (RBRK) leadership • Q1 2026

    Question

    John DiFucci from Guggenheim Partners noted that Rubrik's strong results seem to defy the uncertain macroeconomic backdrop that has suppressed spending for other security companies, and asked for commentary on the demand environment and Rubrik's execution.

    Answer

    Co-Founder, CEO & Chairman Bipul Sinha attributed Rubrik's performance to its creation of the cyber resilience market, which he contrasted with the traditional 'whack-a-mole' approach of buying numerous prevention and detection tools. He stated that cyber resilience is a top priority for CIOs and CSOs, making Rubrik's platform a non-optional, quantum shift in security posture rather than an incremental tool. Sinha affirmed that the demand environment remains strong and that Rubrik is not opportunity or market constrained, given its position in a $50 billion market.

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    John DiFucci's questions to Rubrik Inc (RBRK) leadership • Q4 2025

    Question

    John DiFucci highlighted the impressive top-line and cash flow results but questioned the guidance for moderating free cash flow in fiscal 2026, especially given the strong Q4 performance.

    Answer

    CFO Kiran Choudary acknowledged the strong cash flow performance. He explained that while top-line scale and operating leverage are key drivers, the timing of collections is also a factor. Choudary noted that Rubrik has experienced gradual billings duration compression (mid-to-high single digits year-over-year) and has assumed this trend will continue. He characterized the fiscal 2026 guidance as a thoughtful starting point for the company's first full year providing an annual outlook.

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    John DiFucci's questions to Rubrik Inc (RBRK) leadership • Q3 2025

    Question

    John DiFucci asked about go-to-market partnerships, referencing field checks that indicate growing engagement with VARs and GSIs, and questioned if this trend was accelerating.

    Answer

    CEO Bipul Sinha confirmed that engagement with VARs and GSIs is increasing and has been a trend for several quarters. He explained that as customers demand cyber resilience, channel partners are bringing Rubrik into more strategic conversations about risk mitigation, which elevates their role from infrastructure providers to cybersecurity advisors. This shift helps partners broaden their scope and strengthen their customer relationships, driving more partnerships with Rubrik.

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    John DiFucci's questions to Okta Inc (OKTA) leadership

    John DiFucci's questions to Okta Inc (OKTA) leadership • Q1 2026

    Question

    John DiFucci from Guggenheim Partners asked if the ongoing decline in Net Retention Rate (NRR) was still due to seat and MAU upsell headwinds, and whether this pressure is expected to ease or persist due to the macro environment.

    Answer

    CFO Brett Tighe confirmed that these headwinds are still a factor and that he expects NRR to 'travel in this range' for now. He indicated that a significant deterioration in the macro environment would create further headwinds, suggesting a stabilization rather than an immediate rebound is the current expectation.

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    John DiFucci's questions to Okta Inc (OKTA) leadership • Q4 2025

    Question

    John DiFucci asked about the level of prudence in Okta's annual guidance, questioning if a change in the business or macro environment prompted the significant guidance increase.

    Answer

    CEO Todd McKinnon attributed the confidence to a "blowout" Q4, highlighting over $1 billion in quarterly bookings and strong large-deal momentum. He stated the macro environment remains consistent but noted that customers are increasingly consolidating on Okta's platform for security and to manage AI agent identities. CFO Brett Tighe added that the guidance philosophy of reducing conservatism continues, and congratulated the go-to-market team on their execution.

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    John DiFucci's questions to Okta Inc (OKTA) leadership • Q3 2025

    Question

    John DiFucci inquired about the preliminary FY'26 guidance, asking how to interpret its level of conservatism now that the additional buffer for the prior year's security incident has been removed.

    Answer

    CEO Todd McKinnon framed the guidance as a balance between optimism for new product momentum and appropriate prudence. CFO Brett Tighe clarified that the significant outperformance in FY'25 guidance was an anomaly due to the high uncertainty following the security incident and should not be expected going forward. He also noted that as a larger company, Okta's growth profile has matured, making comparisons to years past less relevant.

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    John DiFucci's questions to Okta Inc (OKTA) leadership • Q2 2025

    Question

    John DiFucci of Guggenheim Securities, LLC, complimented Okta's strong quarterly results but questioned the conservative guidance for current RPO (cRPO), suggesting it implies a future revenue growth slowdown that seems unlikely and creates negative sentiment.

    Answer

    CEO Todd McKinnon acknowledged the feedback, attributing the prudent outlook to two main factors: the need to conservatively lap last year's security incident and the persistent headwinds from a challenging macroeconomic environment. CFO Brett Tighe added that he looks forward to their continued debate on the topic.

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    John DiFucci's questions to SentinelOne Inc (S) leadership

    John DiFucci's questions to SentinelOne Inc (S) leadership • Q1 2026

    Question

    John DiFucci of Guggenheim Partners asked about the go-to-market evolution from a product-centric to a platform strategy, its impact on sales timing, and whether this transition contributed to the quarter's results.

    Answer

    CEO Tomer Weingarten described the go-to-market shift as a continuous evolution rather than a specific Q1 event. He stated that the move to a platform sale with flexible consumption models is a net positive that should improve efficiency, despite ongoing complexities in training and enablement.

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    John DiFucci's questions to SentinelOne Inc (S) leadership • Q4 2025

    Question

    John DiFucci noted that new ARR showed slight growth and asked for more color on why SentinelOne expects to perform better against a consistent macro backdrop in the coming year.

    Answer

    Barbara Larson (CFO) highlighted the improved new business growth in H2 FY25 and expects the trend to continue, with the FY26 net new ARR guide of ~$200M representing 2% YoY growth despite a ~$10M headwind from retiring a legacy product. Tomer Weingarten (CEO) added that strong platform adoption, a ramped sales force, and significant traction with AI solutions (over 300 AI deals in Q4) are key drivers of this confidence.

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    John DiFucci's questions to SentinelOne Inc (S) leadership • Q3 2025

    Question

    John DiFucci asked about SentinelOne's performance in the SMB and mid-market segments, noting that these areas typically have shorter sales cycles and could show momentum more quickly.

    Answer

    CEO Tomer Weingarten confirmed that the SMB and mid-market segments are performing well with increased momentum, highlighting the strong growth of MSSP partners. He noted that the benefits of the current environment are being seen across all segments and geographies, and that the acceleration in the core endpoint market is particularly encouraging.

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    John DiFucci's questions to SentinelOne Inc (S) leadership • Q2 2025

    Question

    John DiFucci of Guggenheim Securities asked if the company plans to redirect its go-to-market strategy to capitalize on the competitor's recent issues and whether its stance on not chasing marketing investment has changed.

    Answer

    CEO Tomer Weingarten responded that the company's existing strategy, which focuses on net new business generation and strengthening its channel ecosystem, aligns well with the current market opportunity. He stated there is no significant change in approach, viewing the situation as an accelerant to the strategy already in place. He emphasized that the company now has the discipline, systems, and processes to execute effectively.

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    John DiFucci's questions to Cyberark Software Ltd (CYBR) leadership

    John DiFucci's questions to Cyberark Software Ltd (CYBR) leadership • Q1 2025

    Question

    John DiFucci sought further detail on the guidance, asking if the embedded conservatism stemmed from specific customer conversations or was a reaction to general macroeconomic news.

    Answer

    CFO Erica Smith and CEO Matt Cohen clarified that customer conversations remain 'incredibly positive' and that the conservative guidance is a prudent measure against broad macro uncertainty, such as potential tariffs, rather than a reflection of any negative customer feedback. They noted it was a responsible decision not to pass the full Q1 beat through to the annual forecast.

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    John DiFucci's questions to Akamai Technologies Inc (AKAM) leadership

    John DiFucci's questions to Akamai Technologies Inc (AKAM) leadership • Q1 2025

    Question

    John DiFucci asked about Akamai's strategy to ramp up new channel partners for its faster-growing security products like Guardicore and API Security, and whether these new channels could also be leveraged to sell its broader infrastructure security portfolio.

    Answer

    CEO Dr. Tom Leighton confirmed that these products are sold through different channels than Akamai's traditional CDN partners, listing examples like Presidio, Optiv, and WWT. CFO Ed McGowan added that 80-90% of new logo acquisition comes through the channel. Both executives affirmed that these partners can and do sell the entire security platform, often leading with Guardicore or API Security and then expanding the relationship.

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    John DiFucci's questions to Akamai Technologies Inc (AKAM) leadership • Q4 2024

    Question

    John DiFucci sought confidence in Akamai's ability to accelerate revenue growth to 10% from the current 3-4% guidance, asking if it's just a matter of math. He also asked for more detail on the profitability and competitive advantages of the compute business.

    Answer

    CFO Ed McGowan explained the acceleration path involves the delivery business drag moderating, security growing durably at 10%, and compute reaccelerating after a near-term transition. CEO F. Leighton detailed compute's advantages: lower egress costs due to efficient data handling, superior performance from a highly distributed platform, and the ability to run containers in hundreds of cities, all leading to better performance at a lower price than hyperscalers.

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    John DiFucci's questions to Workday Inc (WDAY) leadership

    John DiFucci's questions to Workday Inc (WDAY) leadership • Q4 2025

    Question

    John DiFucci of Guggenheim asked if Workday's performance is now more sustainable and if it's positioned to emerge stronger when the macro environment improves, also inquiring about Global Payroll Connect.

    Answer

    CEO Carl Eschenbach affirmed this view, pointing to successful initiatives like driving AI and FINS SKUs, strong full-suite adoption (over 30% of new business), and partner contribution (over 15% of new ACV). Chief Product Officer David Somers added that Global Payroll Connect has been in 150 deals since its October launch, showing strong early traction.

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    John DiFucci's questions to Arm Holdings PLC (ARM) leadership

    John DiFucci's questions to Arm Holdings PLC (ARM) leadership • Q3 2025

    Question

    John DiFucci asked for a high-level perspective on how AI training optimizations, such as those seen with DeepSeek, impact Arm's overall opportunity in the AI market.

    Answer

    CEO Rene Haas described such optimizations as a positive for the industry and for Arm. He argued that more efficient inference lowers costs and expands the total demand for compute, which is especially beneficial for Arm's sweet spot in power-constrained devices like phones and cars. He added that massive spending by cloud players shows the industry is still far from reaching AI's full potential.

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    John DiFucci's questions to Arm Holdings PLC (ARM) leadership • Q2 2025

    Question

    John DiFucci sought more clarity on the Armv9 mix, asking if its growth is expected to continue and what might cause it to stall, given its current concentration in specific market segments.

    Answer

    CEO Rene Haas stated that v9 adoption growth is 'quite predictable' and guaranteed the 25% mix would be 'considerably higher' in a year. He cited growth drivers across PCs, the 'waterfall' of v9 into mid-range mobile, and 100% v9 adoption in the data center. CFO Jason Child added that the quarterly flatness was a temporary mix issue due to strength in the mid-range smartphone market, which has not yet transitioned to v9.

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    John DiFucci's questions to CrowdStrike Holdings Inc (CRWD) leadership

    John DiFucci's questions to CrowdStrike Holdings Inc (CRWD) leadership • Q3 2025

    Question

    John DiFucci requested a clearer explanation for why the historically tight coupling between ARR and revenue is temporarily diverging.

    Answer

    CFO Burt Podbere clarified that the divergence is temporary and primarily caused by the structure of the Customer Commitment Packages (CCPs). He explained that when a CCP includes extended contract time, it creates an immediate impact on ARR, whereas the corresponding revenue is recognized over the life of the contract, causing a short-term lag and decoupling of the two metrics.

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