About Me
Ruby Raley is a senior go-to-market and revenue leader with more than two decades of experience scaling B2B technology businesses across healthcare, logistics, and enterprise software. She partners with founders, operators, and investment teams to accelerate growth, professionalize commercial execution, and translate strategy into measurable results.
Ruby brings a rare blend of sales leadership, product marketing, and customer operations expertise. She has led global GTM initiatives, rebuilt underperforming sales organizations, launched new vertical strategies, and supported complex enterprise deals spanning SaaS, integration platforms, managed services, and compliance-driven solutions. Her background includes senior leadership roles at Axway, Edifecs, Descartes and Cardinal Health, as well as extensive work advising founder-led and PE-backed companies.
As a fractional executive with Five Experts, Ruby focuses on value creation at the inflection points that matter most: clarifying ICP and positioning, aligning sales and marketing execution, improving forecast reliability, strengthening customer onboarding and retention, and enabling management teams to scale without adding unnecessary complexity or cost. She is known for practical execution, data-driven decision-making, and a direct operating style that resonates with both boards and frontline teams.
Ruby is also an active advisor to early and growth-stage companies, a frequent speaker and writer on go-to-market strategy, AI, and operational scale, and a long-time advisory board member to minority-owned and founder-led firms. She holds a Master’s degree in Systems Analysis and Business and has built and led teams across North America, EMEA, and APAC.
Areas of Focus
· Go-to-Market & Commercial Strategy
· Sales Transformation & Enablement
· Product & Solution Marketing
· Customer Operations & Retention
· Founder & Management Team Advisory
· Healthcare and Logistics Technology
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Common Questions
How does a 1-on-1 consultation work?
Connect with leading experts in our network. Simply browse expert profiles, select the ideal advisor for your needs, and schedule a 1-on-1 video session. At your scheduled time, join the live video call to discuss your specific challenges and receive personalized, actionable guidance.
What can I expect to achieve from a single consultation?
While the outcomes vary depending on your specific needs and the expert you consult, you can generally expect to gain actionable insights, practical strategies, and clarity on how to address your growth challenges. Many clients leave with a clear roadmap and next steps.
What information should I provide beforehand to make the session productive?
To maximize the value of your session, we recommend providing the expert with relevant background information about your company, your specific challenges, and your goals for the consultation. This may include documents, data, or key questions you'd like to discuss. The specific requirements can often be communicated directly through our platform's messaging system before the scheduled call.
What is the format of the consultation?
The format is primarily a direct, 1-on-1 discussion tailored to your needs. Experts will use their experience to provide the most effective guidance, which may include a combination of Q&A, strategic discussion, and the presentation of frameworks or best practices. It's designed to be highly interactive and solution-oriented.
How long is a typical consultation?
Session lengths are determined by the expert, and you'll see the duration clearly stated when you book. This allows experts to structure their time effectively to address your needs.
What platform is used for virtual consultations?
Five Experts provides a secure and integrated video conferencing platform for all consultations. This ensures a seamless and professional experience for both growth companies and experts. Details and access are provided upon booking.
Is there any follow-up after the consultation?
Follow-up is at the expert's discretion. We encourage you to discuss potential follow-up options, such as additional sessions or post-session materials, directly with the expert during your consultation.
Can the consultation be tailored to my specific needs?
Yes, consultations are designed to be highly tailored. Before the session, you'll have the opportunity to communicate your specific needs and objectives to the expert, ensuring the session addresses your unique challenges.
Why are Experts doing this?
Many experts on Five Experts are drawn to our mission: to connect those seeking growth with the precise guidance they need, fostering a stronger business ecosystem. They value the opportunity to share their experience, support others in their growth journey, and contribute to the success of ambitious companies. Five Experts provides a user-friendly platform that simplifies these connections, ensuring experts are fairly compensated for their time.
What are the next steps after I book a consultation?
After booking, you'll receive a confirmation with the session details, including the date, time, and video conferencing link. You may also receive instructions on any preparatory materials to provide to the expert. Our platform will guide you through each step to ensure a smooth process.
What is your cancellation or rescheduling policy?
Five Experts has a cancellation and rescheduling policy in place to protect both growth companies and experts. Sessions may be canceled or rescheduled with at least 24 hours’ notice. Growth Companies who cancel within 24 hours of a scheduled session may be charged the full session fee. Experts are also expected to provide at least 24 hours’ notice if they need to reschedule. No-shows or last-minute cancellations may result in a forfeited session or payment, at the discretion of Five Experts. For assistance, please contact us at hi@fiveexperts.com.
What are the timezones the sessions are in?
Five Experts facilitates connections between experts and growth companies across the globe. Therefore, sessions can take place in any timezone. When you schedule a session, you'll see the expert's availability in the time zone chosen within your dashboard, making it easy to find a time that works for both of you. Our platform shares the timezone to ensure a smooth scheduling process.
Do you support international customers?
Yes, Five Experts supports international customers. Our platform is designed to connect growth companies and experts from all over the world. We handle time zone differences, and our platform supports various currencies to facilitate transactions between users in different countries.
When do Experts release their schedule for more sessions?
Expert session availability varies. Some experts update their schedules weekly, while others do so monthly. To secure your preferred time, we recommend booking sessions as early as possible. Don't miss out on the opportunity to connect with the experts you need!
Do you have any guarantees?
We're confident you'll value your first session. However, if it doesn't meet your expectations, please let us know, and we'll work to make it right.