The New Normal Fund

The New Normal Fund / Allison Pickens Ventures Research Investment Thesis The New Normal Fund (now operating as Allison Pickens Ventures) is a solo-GP venture capital fund run by Allison Pickens, the former COO of Gainsight, that partners with B2B AI founders by functioning as a fractional COO and go-to-market architect rather than a traditional finance-first investor. Pickens leverages her experience scaling Gainsight from $1M to $85M ARR and her expertise in customer success, go-to-market strategy, and operational excellence to provide board-level strategic guidance and tactical support to early-stage AI companies. Investment Focus & Thesis Allison Pickens invests in early-stage B2B AI and data infrastructure companies. Her core thesis centers on the intersection of artificial intelligence, go-to-market excellence, and operational maturity. She specifically targets founders building: B2B AI applications - Enterprise software powered by artificial intelligence Data infrastructure - Tools and platforms for data processing and analytics SaaS companies - Recurring revenue business models with strong unit economics As stated on her website: "Scale your AI startup by putting humans first." This reflects her philosophy that success comes from combining AI capabilities with strong human-centric go-to-market strategy and operational excellence. Stage Focus & Check Size Allison Pickens invests across seed-stage companies with a specific check size distribution: Primary focus : $400K-$1M seed-stage investments in AI applications Secondary : $250K-$500K pre-seed investments for exceptional technical founders Occasional : $250K-$500K Series A follow-on investments through her opportunity fund She previously ran The New Normal Fund as a rolling fund for four years and now invests through her personal vehicle (Allison Pickens Ventures) while maintaining her public investment commitments. Lead vs Follow Tendency Allison has both lead and follow capabilities: Leads : She actively leads seed rounds and pre-seed investments, writing checks as the first institutional investor Follows : She participates in oversubscribed rounds by carving out allocations when she has conviction Network leverage : She syndicates portions of her rounds through a network of 20+ CEO and operator LPs who serve as informal advisory boards for portfolio companies Recent Activity & Fund Status The New Normal Fund (as documented on Crunchbase and other platforms) has made 33+ investments. Recent activity indicates: Fund Status : Actively deploying capital (as of January 2026) Latest investments : Recent investment in Waldo (Seed, September 2025), Dealops (Series A, August 2025) Portfolio stage : Primarily seed, with occasional Series A follow-ons Deployment pace : Regular investments throughout 2025 Allison's personal involvement has expanded from just capital to deep operational support, making her one of the most value-add angel/seed investors in the B2B AI space. Portfolio Highlights Allison Pickens has invested in a portfolio of companies including: Notable Public Portfolio Companies: dbt Labs - Modern data transformation tool (board director) Commvault - Data management (holds $441K+ in public shares as of September 2025, NASDAQ: CVLT) Eppo - Feature flagging/experimentation platform (acquired by Datadog for large exit) Mural - Digital whiteboarding and collaboration platform Rainforest QA - Software testing platform (board director) Other Notable Investments: Gamma - Generative AI presentation tool Tennr - B2B AI company (backed by a16z) Modal - Serverless compute platform for AI EvenUp - Legal AI platform Norm AI - AI-powered customer success platform Hightouch - Reverse ETL and activation platform Scribe - Process documentation automation Lumos - Identity governance platform (Series B, $85M from a16z and Scale) Vitable - Healthcare startup (scaled from pre-seed to $6M ARR) Fastrak AI - Enterprise platform Arketa - Operations/finance platform Parable - Business operations platform XBuild - Enterprise platform (backed by a16z) Mux - Video infrastructure Fairmarkit - B2B software AbstractOps - Operations platform Pocus - Product engagement platform Solea - ERP/operations platform (pre-seed) Glimpse - BI/analytics platform (backed by 8VC) Boast AI / Fincraft - Pre-seed companies Inventive - Tech company (backed by Wing VC) TextQL - Data query tool Opvia - ~$1M ARR operations platform Dooly - Sales operations platform Krane, Clarify (Dover), Assort Health - Other portfolio investments She has invested in approximately 30% of the Enterprise Tech 30 early/mid-stage companies. Geographic & Sector Focus Geographic: Primarily United States, with focus on SF Bay Area and other tech hubs Sectors: The portfolio shows deep focus on: Enterprise software and SaaS AI/ML applications Data infrastructure and platforms Operations/business automation Health tech Fintech Team & Decision Making Solo-GP Model: Allison Pickens operates as the sole general partner Decision-making is individual (not committee-based) She moves with conviction and doesn't require consensus Very responsive and hands-on decision timeline (10-minute response times cited by founders) Advisory Network: 20+ CEO and operator LPs serve as informal advisory board members Extensive network in Silicon Valley and beyond Deep relationships with executives, board members, and founders Involvement & Support Model Unlike traditional VCs, Allison provides deep operational involvement: Fractional COO role : Go-to-market strategy, customer success, operational excellence Board-level guidance : Strategic thinking without necessarily requiring board seats GTM expertise : Sales, customer success, pricing, expansion strategy, OKR development Executive coaching : Leadership development, hiring, organizational design Network access : Introductions to customers, executives, other investors, operational talent Regular check-ins : Monthly or more frequent meetings with portfolio companies Proactive support : Not waiting to be asked; reaching out to offer help Founders consistently note she is "the most value-add non-lead investor on cap table" and deliver 10x return on dollars invested in terms of value. Founder Preferences Allison backs founders who demonstrate: Technical excellence : Deep understanding of their domain Operational mindset : Focus on unit economics, growth efficiency, and ARR Coachability : Openness to advice and strategic guidance Founder-first approach : Putting team and founders first, not just maximizing returns Category creation potential : Building transformational companies in underserved categories AI/data expertise : For companies in AI/ML or data infrastructure, deep technical knowledge As stated by one CEO: "She has extraordinary ability to see around corners and challenge you to think bigger while staying ruthlessly focused on what drives outcomes." Warm Intros & Decision Process Warm introductions : Highly preferred and common (she leverages her extensive network) Decision timeline : Fast - extremely responsive investor who can move quickly Decision process : Solo GP means faster decisions than committee-based funds Conviction-based : She moves when she has conviction, not when trying to make consensus Notable Recognition & Background Allison Pickens Background: Former Chief Operating Officer of Gainsight (scaled from $1M to $85M ARR) Built 250-person team at Gainsight Board Director at dbt Labs (a16z, Sequoia backed) Board Director at Commvault (NASDAQ: CVLT) - one of youngest public company directors Former EIR at Bessemer Venture Partners Senior Advisor at Boston Consulting Group (BCG) Author: "The Customer Success Economy" (Wiley) Host: The Customer Success Podcast (100K+ listeners) Published 100+ thought leadership pieces on recurring revenue and customer success Recognition: Top Women in SaaS, Top 50 People in Sales, Top 25 Customer Success Influencers Investment Philosophy: "Putting humans first" approach to AI Believes in building category-defining companies Focus on operational excellence and go-to-market as sustainable competitive advantages Long-term value creation over quick exits Genuinely cares about founder success and company building Why Founders Work With Allison Consistent themes from founder testimonials: She delivers - Most helpful investor on cap table, often writing smallest check but providing outsized value Accessible - Responds within 10 minutes, always available for advice and strategy Experienced - Scaled a company to unicorn status, built teams, navigated exits Network effect - Introductions that carry weight with customers, candidates, and investors Hands-on - Actively engaged in solving business problems, not passive investor Authentic - Genuinely interested in founder success as person, not just return maximization One founder called her "the first person I'd try to convince to invest in my next company." Summary The New Normal Fund (Allison Pickens Ventures) represents a new model of venture investing focused on operational excellence, go-to-market strategy, and human-first AI development. Rather than traditional finance-first investing, Allison positions herself as a fractional COO and trusted advisor who brings decades of scaling experience, a powerful network, and genuine commitment to founder success. Her portfolio of 30+ companies, many with significant exits or unicorn status, demonstrates the effectiveness of this approach. She is best reached through warm introductions given her network-based sourcing model.