Leslie Greenwood

Chief Evangelist, Community Strategist, Co-Founder of Wednesday Women, Startup Advisor, Ex-Stay-At-Home Mom

I'm the Co-Founder of Wednesday Women and the Founder of Chief Evangelist Consulting: two ventures grounded in a core belief: community isn’t a tactic, it’s a force.

Wednesday Women began as a ripple in 2023 as a small, intentional effort to elevate executive women. We amplify women’s voices on LinkedIn, on stages, on podcasts, not as polished personas, but as their real, remarkable selves (the woman behind the title). Our public platform is for everyone, and we’ve built a private membership for executive women who want to go deeper with that mission and create connections both help unlock challenges but also are their biggest cheerleaders. 

Through Chief Evangelist Consulting, I help companies design community strategies that create lasting engagement. With 20+ years in customer-facing leadership roles, I approach community as a strategic lever, rooted in trust, value, and connection.

At the heart of everything I do is a belief in the power of evangelism, authenticity, and shared momentum.

And yes — I run on coffee, dark chocolate, trying (and failing) to keep me very vocal dog in check and talking loudly about diversity in tech.

Ambassador

Advocating for Pavilion’s mission of helping every leader and their team achieve their professional potential through community-powered learning. I will be supporting key initiatives, developing and teaching curriculum for Pavilion University and providing over 10,000 members with leadership advice. Join us at joinpavilion.com.

I’ve been seeing a trend….
more women walking away from corporate life to go fractional, consult, or build their own thing.

And I get it.
I did too.

At some point, I realized I’m “consciously unemployable”. 

That’s a choice. 

Not because I can’t play the corporate game (well actually if you know me, I can’t 🤣), but because I finally saw how much of it was built on rules that were never written for us. And I was done building others’ dreams.  

As Sarah Allen-Short wrote,  

“Liberal feminism didn’t ruin the workplace. It exposed it.”
(If you read the NYT article, you’ll get the reference.)

What we’re watching isn’t women giving up. It’s women waking up.

“Lean In” taught women to play the old game. This era’s about building a new one.

When you realize the system was never designed for you, you start creating something better.

(📸: Quote from Sarah’s Substack Work Doula — worth the read.)

 #futureofwork #womeninbusiness #founderlife #fractionalleadership

Leslie Greenwood 

💜 Shining the Spotlight on Exec Women, Co-Founder of Wednesday Women, Community Strategist, Chief Evangelist, Startup Advisor, Ex-Stay-At-Home Mom

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Andrea 🤓 Lechner-Becker and Raja Walia arguing just made my morning!  

That’s all, that’s the post. 💜 

And yes, Erin Kasmarick is still the HubSpot wizard 🧙‍♀️! We 💜💜💜💜her.

AI can’t invent weird. It can’t really do different. This is still where humans have the competitive advantage 

Think about Apple’s “1984” ad.
Or, Coinbase’s random bouncing QR code.

No robot’s out here dreaming those up. 

Those ideas hit because they were so human. Unexpected. Odd.
The kind of weird that makes you stop scrolling and go, “Wait, what?”

That’s what AI can’t fake.

It can totally take your ideas and scale them. But if what you feed it is already kinda basic… it’s just going to spit out more basic.

What’s that mean for us humans? Creativity actually matters more now. Because AI’s like this giant volume knob. Whatever you give it, it just cranks it up.

Bottom line: The magic happens when a human is brave enough to think weird.

We unpack this (and a few more “AI vs. human creativity” hot takes) in the full episode.
Catch it here → https://lnkd.in/gCvusPW6

#MarTech #Marketing #GTM #RevOps #AI

Susan Whittemore

tax.com™

Tax.com™ solutions are powered by the insights and ingenuity of some of the most renowned tax professionals at Ryan, LLC whose experience and expertise form the bedrock on which our solutions are built. The result is responsive, intelligent technology that empowers organizations to act quickly and confidently within a dynamic tax landscape. Harness the power of tax.com™ solutions and take your organization into the future.Tax.com™ solutions are powered by the insights and ingenuity of some of the most renowned tax professionals at Ryan, LLC whose experience and expertise form the bedrock on which our solutions are built. The result is responsive, intelligent technology that empowers organizations to act quickly and confidently within a dynamic tax landscape. Harness the power of tax.com™ solutions and take your organization into the future.

VP, Revenue Operations

Hunters and Unicorns

Strategic Partner

QFlow.ai

QFlow leverages AI and advanced analytics to offer ready-to-use GTM stats, performance driver analysis, and scenario planning capabilities. Our vision is to equip every B2B company with the power of a robust 10-person GTM Finance team (including BI analysts and data engineers).

GTM and Revenue Operations Executive Advisor

Teampay

➼ Led Revenue Operations, optimizing GTM tech stack, streamlining tool integrations, and elevating cross-functional productivity.
➼ Established a comprehensive end-to-end process from Marketing to Customer Success, embedding feedback loops and key conversion and velocity metrics.
➼ Collaborated with CFO and CRO to define and harmonize crucial SaaS metrics (ARR, MRR, NRR, GRR, etc.), boosting operational efficiency and customer satisfaction.
➼ Secured advantageous vendor contracts, and managed data insights for board presentations, enhancing strategic decision-making.
➼ Implemented robust internal controls across marketing, sales, and post-sales phases ensuring data-driven transparency in GTM strategies and campaigns.

About Teampay:
Teampay is a leader in distributed spend management, providing businesses with unmatched spending oversight and empowering employees in procurement. We believe in channeling efforts towards growth over overhead.

Head of Revenue Operations

Starburst Data

➼ Revolutionized the GTM strategy and tech stack, centralizing cross-functional teams with agile methodologies to enhance both sales-marketing synergy and customer satisfaction.
➼ Leveraged PXT Select in recruitment to expedite the hiring process, ensure candidate fit, and personalize our sales coaching methods, culminating in a diverse, elite global sales team.
➼ In partnership with the VP of Sales, redefined the operating rhythm, achieving increased forecast accuracy and a cohesive, transparent forecasting process from frontline teams up to the CEO.
➼ Oversaw sales and marketing KPIs, paving the way for scalable pipelines, strategic territory planning, and propelling the company towards significant milestones like Series C Funding.

About Starburst Data:
Starburst champions the vision of unveiling the unseen for its customers. Over a decade, our founders, across three ventures, tackled data access challenges, traditionally deemed slow and inflexible. Starburst presents a solution, counteracting data silos and ensuring swift access. We amplify open source Trino's capabilities, a rapid distributed analytics engine, by integrating essential connectors, fortifying security, and ensuring 24x7 support for expansive, rapid data access.

VP, GTM and Revenue Operations

Silk

➼ Drove Silk's transition from hardware-centric to software powerhouse, overseeing comprehensive operational overhauls and reimagining the go-to-market strategy.
➼ Implemented Command of the Message and MEDDICC methodologies across all levels, resulting in a remarkable 30% sales increase.
➼ Directed a rigorous training program for sales reps, leading to improvements in pipeline velocity (25% up), sales cycle duration (20% reduction), and win rates (15% growth).
➼ Revamped the marketing funnel, achieving a 40% pipeline boost and a significant 25% revenue increase through data-driven territory planning and optimized lead strategies.
➼ Collaborated closely with top-tier leadership, including the COO, SVP of Sales, and CMO, on objectives, technological transformations, and seller adaptations, in alignment with Force Management's strategies.

About Silk:
Emerging from its earlier avatar, Kaminario, in 2020, Silk's Cloud Data Platform is the touchstone of cloud efficiency. It empowers entities to extract tenfold performance from their cloud data while incurring 30% fewer costs. Positioned between application stacks and cloud infra, it elevates the entire cloud ecosystem without modifications. With features like real-time data reduction, thin provisioning, and perpetual resource tuning, Silk tailors your cloud spending to match evolving data needs, making cloud economics more viable.

Sr. Director, Global Revenue Operations

Perfecto Mobile

➼ Drove substantial revenue growth, taking ARR from $13M to $75M.
➼ Expanded and operationalized the enterprise sales team, growing it from 4 to 60+ global sellers, focusing on enterprise value selling in tandem with the CRO.
➼ Oversaw comprehensive new hire training and enablement, ensuring consistent skill development and tool accessibility, incorporating MEDDICC & Command of the Message for optimal sales performance.
➼ Crafted an all-encompassing go-to-market strategy, utilizing both direct and indirect sales channels, in-house sales initiatives, and SDRs, while handling compensation plans for various teams.
➼ Streamlined the MEDDICC-based forecast process, providing vital sales KPI insights to the CRO and Managers for informed strategic decision-making.
➼ Directed global sales operations and development, encompassing sales forecasting, Salesforce operations, onboarding, renewals management, and business development while fostering team cohesion through events like Sales Kick Offs and Quarterly Reviews.

About Perfecto Mobile:
Perfecto Mobile offers industry-leading mobile and web automation testing solutions. We facilitate efficient testing, monitoring, and delivery of high-quality applications, supporting multiple frameworks including Selenium and Appium.

AVP, Sales Operations and Sales Development 

Rocket Software

My Role:
➼ Drove substantial growth at Rocket, increasing ARR from $200m to $500m and doubling the workforce from 600 to 1,200+.
➼ Unified 15+ distinct brands through innovative tools and systems, enhancing insight selling and fostering organizational synergy.
➼ Pioneered Rocket's first-ever sales meetings, laying the groundwork for sustained growth and cross-team collaboration.
➼ Integrated a unified sales CRM platform using Salesforce and Marketo, streamlining operations across diverse business units and refining sales processes.
➼ Designed a robust lead-to-order framework, covering lead management, CPQ, forecasting, and insight selling tools.
➼ Secured the Prosci Change Management Practitioner certification, underscoring a dedication to efficacious organizational transformation in complex growth scenarios.

About Rocket Software:
Rocket Software, a leading partner to global enterprises, addresses multifaceted IT challenges spanning infrastructure, data, and applications. Dedicated to in-place modernization through a hybrid cloud approach, Rocket assists over 10,000 customers globally. Its expansive team of 2,600 accelerates and refines modernization paths, meeting evolving market demands. Based in Boston and part of the Bain Capital Private Equity portfolio, Rocket's global centers of excellence cater to diverse clientele.

Global Sales Operations and Enablement Director

Novell

➼ Supported the VP, Americas, providing senior executive assistance as he rose through the ranks to ultimately assume the role of CEO.
➼ Expanded my Sr. Executive support to top-tier executives including the CFO, General Counsel, and SVP of HR, while also managing critical board committees.
➼ Launched the global onboarding portal on time and within budget, elevating productivity for new hires by an impressive 50% within the first quarter.
➼ Partnered closely in reshaping the Americas go-to-market strategy, leveraging transformational emotional intelligence, which led to a 13% increase in operating profit over two years and set new benchmarks in revenue growth.
➼ Jointly penned the M&A Integrations Playbook, refining Novell's approach to integrations and acquisitions.
➼ Served as a trusted internal consultant, addressing pivotal challenges like employee retention and skill development, laying the foundation for a vibrant and high-performing work environment.

About Novell:
Novell, Inc., operational between 1980 to 2014, was a renowned American software and services entity based in Provo, Utah. Its flagship product was the versatile network OS, Novell NetWare.

Sr. Executive Support & Project Management

Deloitte & Touche

➼ Started at Deloitte & Touche at 18 following the acquisition of their own start-up, Real Estate Tax Services, Inc.
➼ Partnered closely with the Boston-based leadership and the Partner-in-Charge, showing adaptability by operating out of two major locations: Boston, MA, and Manchester, NH.
➼ Successfully managed a $25M property tax liability portfolio, emphasizing compliance and financial risk mitigation.
➼ Pioneered the development of AtlasTax, a cutting-edge property tax CRM, ushering in a new era of client tax management for Deloitte & Touche.
➼ Rapidly advanced to pivotal roles such as East Region Consultant and Account Manager.
➼ Championed AtlasTax's adoption, enhancing client satisfaction and strengthening business partnerships through strategic presentations and demonstrations.

About Deloitte & Touche:
Renowned as the world's fourth-largest public accounting entity, Deloitte & Touche stands tall among the Big Six accounting magnates. Delivering a plethora of professional services, from accounting, auditing to tax and management consulting, its vast network spans 15,300 professionals across 100+ U.S. cities. As a constituent of Deloitte Touche Tohmatsu International, it amplifies its global footprint, making a mark in managerial consulting via 56,000 professionals spread over 108 countries.

Account Manager - Tax Associate

GTM Leader | Revenue Operations Executive

A transformative Revenue Operations Executive and GTM leader with over 15 years of experience. My passion lies in building elite sales teams and driving operational efficiency to scale businesses. 

Here's how I make an impact

➥Strategic Leadership: Spearheaded GTM revamps and sales optimizations in top-tier tech firms.

➥Operational Excellence: Streamlined processes from onboarding to customer journey, reducing friction and elevating performance.

➥Data-Driven Agility: Accelerated insight-driven decision making, ensuring speed, agility, and alignment across leadership teams for rapid strategic adjustments.

➥Team Building: Utilized PXT Select, DiSC, and Predictive Index for efficient hiring and tailored sales coaching, creating diverse, high-performing teams.

➥Innovative Solutions: My approach combines strategic technology application with a focus on buyer journey insights, ensuring growth and efficiency.

Revenue Operations - Consultant

Operations Consulting Services:
Onboarding, Buying-to-Customer Journey Mapping, Process Design and Workflows, LinkedIn Strategies, RevOps Strategies, Prioritization Workshops, and ICP definition / validation.

Personal Coaching Services:
Career Mapping and Pivots; Professional Branding, LinkedIn Workshops, Unstucking Yourself, Team Building, and Clarity / Prioritization Workshops.

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The Battle

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Susan Whittemore

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Leslie Greenwood's LinkedIn Performance

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