Ever watched an AI chatbot confidently give the wrong answer, then trap customers in a loop they cannot escape?
The knowledge base looks complete. The tech stack glows on vendor slides. Yet customers still screenshot broken chats and escalate on social. Agents scramble, leaders drown in dashboards, and no one owns the end-to-end experience.
This is the chaos that fractional Chief Customer Officer Alana D’Angelica steps into. With over 20 years in customer success, support, and operations, she has led B2B and B2C teams at Indeed, Datto, and Wix, growing global organizations from small pods to more than 550 people while protecting both revenue and humanity in the process.
Fractional Chief Customer Officer: When “smart” CX breaks
Today, Alana partners with fast-moving tech startups, SMBs, and non-profits as a fractional CCO and customer success consultant. She helps founders and executive teams design scalable, customer-centric journeys, build durable recurring revenue, and turn overwhelmed frontline teams into confident advocates. Whether the context is subscription SaaS, marketplaces, or mission-driven services, her lens combines operating rigor, customer empathy, and executive-level storytelling that boards understand.
In this exclusive CXQuest.com interview, Alana unpacks what it really takes to move from “we respond to tickets” to “we orchestrate value,” especially when AI, automation, and cost pressure collide. The conversation starts with on-the-ground wins and then moves into frameworks, metrics, and tough trade-offs that every CX and CS leader now faces.
Why Most Surprising Customer Success Wins Matter?
Q1. What CX or customer success win in your career surprised you the most, and why did it matter to the business?
AD: One of the most surprising wins was seeing how quickly retention improved once we clearly defined ownership and accountability across the customer journey. I’m obsessive about clear processes and scalable operations. In multiple organizations, churn wasn’t caused by product failure, but by customers falling through the cracks. This starts with a deep journey mapping exercise. Once we operationalized onboarding, adoption, and renewal ownership, retention improved faster than expected, and revenue stabilized without major product changes.
Q2. When you walk into a new startup or SMB as a fractional CCO, what are the first signals you scan to understand customer health?
AD: The first thing I assess is whether the company has clearly defined processes across the customer journey: onboarding, adoption, renewal, and advocacy. If those exist, I look at how success is measured at each stage, including engagement metrics, customer satisfaction, renewal rates, expansion rates, and NRR.
While churn rate is critical, it’s a lagging indicator and doesn’t explain why or when customers decide to leave. That’s why I quickly move deeper into the customer journey to identify breakdowns, friction points, and missed opportunities.
Experience Helps in Scaling Global Support and Success
Q3. How did your experiences at Indeed, Datto, and Wix shape the way you think about scaling global support and success teams from single digits to hundreds?
AD: Mission matters. When large teams are responsible for the customer experience, they need to genuinely believe in the product and its impact. At Indeed, the team rallied around a clear and noble mission: helping people get jobs. Even though we served the employer side, the team felt they were contributing to meaningful outcomes for job seekers, which translated into exceptional customer experiences.
Documentation and training are essential for scale. I’ve seen organizations rely on tribal knowledge and word-of-mouth training, which inevitably creates inconsistent CX. Startups often resist structured processes in the name of speed, only to realize later how costly it is to backtrack. Clear documentation and training enable consistent delivery at scale.
Q4. What early-stage CX or CS decisions do founders often delay, and how does that delay show up later in churn or revenue leakage?
AD: Founders often delay investing in onboarding new customers (they are just so excited about a sale) and general proactive customer success. Most lead with customer support alone. While both functions are necessary, a strong customer success strategy reduces the volume of support issues by proactively delivering value and addressing needs before problems arise. When onboarding and success are underdeveloped, churn increases and expansion opportunities are missed.
Value of a Fractional Chief Customer Officer
Q5. How do you explain the value of a fractional Chief Customer Officer to a leadership team that has never had a CCO before?
AD: A fractional Chief Customer Officer brings executive-level ownership of the customer experience without the cost of a full-time hire. A good CCO will connect Sales, Product and your customer experience and ensure customers adopt, stay, and achieve success with your product. Many companies focus first on acquisition, but do little to retain those customers. CAC is expensive, and a dedicated focus on retention and expansion is the real key to growth. A CCO will help you get there faster.
Q6. When budgets are tight, how do you prioritize between adding headcount, investing in tooling, and redesigning processes in customer operations?
AD: I always start with process redesign. Once the ideal process is defined, I invest in tooling to support and automate it. I then allow time for the process to stabilize and demonstrate impact. Only after that do I recommend adding headcount, ensuring people are scaling a proven system rather than compensating for broken processes.
A Healthy Customer-Centric Partnership in Recurring Revenue Businesses
Q7. What does a healthy, customer-centric partnership between Sales, Product, and Customer Success look like in recurring revenue businesses?
AD: Healthy partnerships include:
Sales: Customer Success should be involved pre-sale. I prefer models where CS has direct interaction before deals close, ensuring alignment between what’s sold and what’s delivered.
Product: Customer Success must play an active role in shaping the product roadmap, and product teams must regularly engage directly with customers. A strong VoC program (outlined below) will help this.
Alignment across these teams ensures a consistent and credible customer experience.
Q8. How do you approach building a Voice of the Customer program so that insights actually influence product roadmaps, not just slide decks?
AD: I’ve approached this in two ways:
First, I have my teams rigorously track customer feedback and needs, tying them to both volume and revenue impact. Each cycle, we provide product teams with clear recommendations focused on improving experiences for the largest customer segments and driving meaningful impact for high-revenue accounts.
Second, we bring the actual voice of the customer to life. Alongside data, we share call recordings, customer quotes, and live demos so product teams can hear and see real customer needs, not just review numbers in a presentation. I also recommend having product teams join customer feedback and advocacy calls directly, so they can hear firsthand what customers are actually saying and ask questions in real time.
What Practical Playbooks to Use?
Q9. What practical playbooks do you use to move a team from reactive firefighting to proactive success planning with customers?
AD: To move teams out of reactive mode, I focus on:
Identifying the most common issues driving inbound requests.
Determining which of those issues can be prevented through better processes, tooling, or education.
As inbound volume decreases, teams must shift to a proactive strategy. Silence from customers does not equal success. Proactive outreach should be purposeful and value-driven, not just “checking in.” The goal is to deliver outcomes customers couldn’t achieve on their own.
Where AI and Automation Add Real Value
Q10. Where do you see AI and automation adding real value to customer success teams today, and where do you draw the line to protect the human experience?
AD: Most teams are still underutilizing AI and automation. At a minimum, real value comes from:
Call recording analysis, note-taking, and insight summarization
Usage data analysis to support QBRs and account preparation
Communication support and consistency
Handoff and continuity between teams
Automated task generation to guide daily execution
There is significant room to grow here. In my work with large organizations, I still see an enormous amount of manual work placed on customer success teams, which undervalues their true potential and keeps them focused on low-impact tasks.
Where to draw the line depends on the company and the product or service. I do see a future where some products can run their customer experience largely through AI, and that will work well. In those cases, there may be human supervisors of AI-led teams (and they themselves be AI-assisted).
However, there are products and services that will always require human connection. That’s where I see the greatest opportunity. As AI removes administrative and repetitive work, humans can spend more time on strategy, problem-solving, and building genuine human relationships with customers, instead of button-pushing, data entry, and other tedious tasks.
Navigating CX and CS Cost Versus Value
Q11. How do you navigate CX and CS cost-versus-value conflicts when leaders push for more automation but customers still need human help?
AD: In practice, I see leaders asking for more automation, but rarely investing enough to truly reduce manual workload. Automation should first eliminate low-value work for teams, not replace meaningful customer interactions. When done correctly, automation enables better human engagement rather than diminishing it.
Q12. Which metrics and leading indicators best prove that a fractional CCO model works and that customer success is truly driving net revenue retention?
AD: Key indicators include improved onboarding completion rates, faster time-to-value, increased product adoption, reduced churn, higher gross and net revenue retention, and measurable revenue saved through proactive intervention. Over time, clearer ownership and improved cross-functional alignment also show up in more predictable renewals and expansion.
Coaching Frontline Managers and ICs
Q13. How do you coach frontline managers and ICs through change when new playbooks, tools, or coverage models disrupt their routines?
AD: Ideally, teams are hired with adaptability in mind. I ask interview questions specifically about how candidates handle change – eg: “You have been running your onboarding process in X, Y, Z way. Tomorrow, we announce that we are changing the process completely and now you have to do A, B, C instead. How do you respond to this change?”
When inheriting teams that weren’t built this way, inclusion is critical. In every major transformation I’ve led, involving top performers in the creation and rollout of new processes led to stronger adoption and better outcomes.
Q14. For non-profits and mission-driven organizations, how does your approach to customer or member experience differ from pure-play SaaS?
AD: My work with nonprofits has focused on donor and member retention, and the fundamentals are really similar to SaaS. Donor relationships require a stronger human and relational approach, while members should be treated as customers with clear value delivery, engagement, and retention strategies. I find that mission-driven orgs require more emotional connection than a traditional SaaS environment, so the engagement and relationship building may include more impact storytelling, and stewardship, not just milestones and metrics.
An Advice to Emerging CS Leaders
Q15. If you could give one piece of advice to an emerging CS leader stepping into their first VP or Head of CS role, what would you ask them to focus on first?
AD: Build a clear team mission and create an environment that embraces change. When teams understand why their work matters and feel supported through change, they can accomplish almost anything. As Dale Carnegie said, “appeal to the nobler motives”. No matter what your product or service is – find a way to get the team connected to the impact it makes, and great CX will follow.
Fractional Chief Customer Officer: From Chaos to Accountable CX
Alana’s journey, as a Fractional Chief Customer Officer, from scaling massive global teams to advising lean, high-growth organizations shows a pattern: customer success becomes truly strategic when someone owns the entire value story, from onboarding through renewal and advocacy. Her work proves that fractional leadership can plug that gap without waiting for a full-time CCO headcount.
For CXQuest.com readers, the big takeaway is that tools and AI only amplify whatever operating reality already exists. If journeys are fragmented, AI will accelerate the confusion. If teams align around shared definitions of value, success plans, and clear customer commitments, AI can extend reach, not erode trust.
Explore more deep dives and interviews on AI in CX, CX leadership, and customer success operating models in the dedicated hubs on CXQuest.com. Use these insights to challenge your own dashboards, reframe success conversations with your C-suite, and design experiences where customers feel guided, not processed. And if you find yourself in the middle of CX chaos, this interview with Alana D’Angelica may be the starting point for a different kind of conversation about what “Chief Customer Officer” really means.
