My 2024 biggest challenges

Hi there,

Last year in January, I transitioned into a Strategic CSM role—a step up in my career that came with new responsibilities and opportunities to learn and grow in a fast-paced, evolving organization.

For more context, in October 2022, Condeco (my previous company) merged with iOffice and SpaceIQ to create Eptura, the leading WorkTech software solution.

2024 was a year of significant change for my organization, brining with it a set of new new challenges:

📍 Navigating my first merger: I’ve heard stories about what mergers do to an organization, but experiencing it firsthand was entirely different. Eptura’s recent merger brought together nine different products and systems, creating a unique environment of rapid change. While this merger introduced opportunities to align processes and systems, it also brought challenges with accessing complete historical customer information and bridging communication gaps.

📍 Balancing customer needs and learning curves: In my new role, I inherited accounts using products I had never worked with before. Balancing the responsibility of supporting these customers effectively while ramping up on unfamiliar products required a focused, adaptable, and intentional approach to prioritize both learning and delivery.

📍 Building strategic executive relationships: As a Strategic CSM, establishing relationships with executive stakeholders is a critical part of the role. However, many accounts I inherited lacked established executive connections, and my initial contacts were limited to day-to-day product admins. I needed to map out key decision-makers, understand their motivations, and align with their strategic goals.

📍 Driving alignment: Without access to previous success plans or business reviews, I had to start from scratch. Aligning with customer teams on goals, outcomes, and strategic priorities became a key focus to ensure every conversation drove measurable value.

📍 Addressing fragmented data: Accurate data is essential for a Strategic CSM to make informed recommendations. Historical inconsistencies and scattered records required me to proactively bridge gaps, consolidate insights, and build a clear picture of each customer’s current state and goals.

I was thankful that my leadership team recognized these challenges and proactively built strategies to support us. Initiatives like Success Planning enablement, executive sponsorship programs, better data and usage reports, and closer collaboration with Product and Sales teams created a foundation that supported my approach.

I knew that to be successful, I needed to focus on what I could control: learning more about my customers, building stronger relationships, and creating systems to deliver consistent value.

While I am not done yet, I’ve made significant progress.

Here is the plan I put together:

1. Start with a discovery mindset:

To understand my customers better, I embraced curiosity and thorough research. I reviewed contracts and product subscriptions, analyzed historical data (when available), and scheduled discovery sessions to ask open-ended questions about their current priorities and challenges.

I also developed a discovery framework by creating a standardized set of questions to guide initial customer conversations and uncover strategic priorities, gaps, and opportunities. My discovery framework focused on three key areas:

• Company research: Understanding the organization’s priorities and structure.

• Industry trends: Identifying broader market trends that may impact customers.

• Stakeholder goals: Uncovering individual stakeholder motivations and success metrics.

Pro Tip: If historical context is limited, ask customers directly about their workflows, pain points, and success metrics. Their answers will often reveal what’s missing.

2. Learn the products—and their value propositions.

With multiple unfamiliar products in my portfolio, I dedicated time to understanding how each solution worked and the business problems it solved. This remains an ongoing process, and I recognize that deep product knowledge takes time.

I collaborated with internal product experts, attended training sessions, shadowed colleagues, and accessed demo environments to learn hands-on. This practical experience significantly accelerated my learning and gave me the confidence to guide my customers effectively.

Pro Tip: Treat product learning as an ongoing process. Regularly revisit resources and stay updated on feature releases to maintain credibility with customers.

3. Build executive relationships strategically.

I prioritized building connections with decision-makers and executive stakeholders. Using Salesforce, I mapped out existing contacts and identified gaps.

To prepare for strategic conversations, I used ChatGPT and other research tools to better understand executive roles and motivations. For example:

• What is the job description of a VP of Real Estate?

• What are the main responsibilities of a VP of Real Estate?

• Which metrics are most important to a VP of Real Estate?

This research helped me align conversations with their priorities and deliver insights tailored to their goals.

Pro Tip: Executives spend time with CSMs who offer actionable insights that align with their success metrics.

4. Create Success Plans as a baseline for value.

With lessons 1–3 completed, I was ready to draft an initial Success Plan. I partnered with my stakeholders to co-create plans that clarified goals, success metrics, and desired outcomes.

I prioritized my top five accounts, creating detailed roadmaps for collaboration. These plans became central to our ongoing conversations, helping us stay aligned and focused on results.

Additionally, I introduced regular business reviews to communicate progress and adjust plans as needed.

Pro Tip: Introduce the Success Plan early, and use it as a living document to drive ongoing conversations about value and priorities.

5. Proactively address data gaps and inconsistencies.

Data clarity was essential to delivering value effectively. I worked closely with RevOps, Product, and Finance teams to address inconsistencies, consolidate insights, and standardize documentation processes.

To ensure long-term improvements, I built stakeholder maps, gathered product usage data, reviewed contract details, and registered customer goals in our Customer Success platform.

Pro Tip: Approach data inconsistencies with curiosity and persistence. Aligning systems may take time, but it’s worth the effort to create clarity.

Final Thoughts:

This role has stretched me in so many ways, but it’s also been a period of incredible growth. 🚀

Navigating my Strategic CSM role in a post-merger environment reminded me of the power of collaboration, curiosity, and persistence. By focusing on discovery, building relationships, and creating tailored success plans, I’ve been able to have more strategic conversations and deliver lasting value.

The good news?

2025 is already looking brighter. I feel more prepared, focused, and equipped to tackle whatever comes next, with clarity and purpose.

What was your biggest challenge from 2024?
I’d love to hear your thoughts.

Best,
Erika

P.S. I am working on my third guide for CSMs: A Success Plan playbook. In this guide, I will dive deeper into these strategies and offer the step-by-step process to build an impactful Success Plan that drives customer growth 🚀.

Stay tuned for the release.