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:

1. She delivers - Most helpful investor on cap table, often writing smallest check but providing outsized value
2. Accessible - Responds within 10 minutes, always available for advice and strategy
3. Experienced - Scaled a company to unicorn status, built teams, navigated exits
4. Network effect - Introductions that carry weight with customers, candidates, and investors
5. Hands-on - Actively engaged in solving business problems, not passive investor
6. 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.