Cristy Maldonado’s Post

I had dinner with a good friend recently who is currently working at a SaaS company that has not been performing well. As I listened to her share her impressions, I thought of the following: You're standing in a crowd. You notice that there's a car driving on the road. At the end of the road, there's a turn, and as the car continues to drive, it doesn't turn. Your gut tells you that the car is going to hit the wall, but you continue to stand there and watch. Sounds ridiculous right? Not really. This is something that many of us "see" every day. Oftentimes, we want to believe that what we are all collectively witnessing isn't happening. We don't want to "see" the "signs". In my experience, I've seen many warning signs, such as: 🛑 No net new sales quarter over quarter for at least 2 quarters in a row 🌂 The sales pipeline is DRY 👎 Teams, like professional services, sit around with nothing to do 👁 No strategic vision for the product/service, which is why it doesn't land with prospects Why is it so hard for people to see these signs? 😍 You truly love your job. You have faith in leadership. 👩💼 You have an important role. You don't want to let that go. 😑 Your job is good enough. You really don't want the hassle of finding a new one. 💪 You have other people counting on you. Here's what I told my friend, and ultimately what I'm sharing with you: If your company is showing the signs I've shared, does it mean that something as terrible as layoffs are imminent? No, but many of them in combination are a good indicator that something isn't right. If you love your job and can't imagine trading it for anything else, I understand. But, if any of the above is making you think twice, start planning now. Start planning now before someone else makes the plan for you. #career #saas #leadership #layoffs

Here's a scenario: 👎 You have a customer that has historically low product usage.  👯 However, when you have a call with this customer, the key stakeholder and the stakeholder's team attend the call. 🎉 The customer realizes that they have work to do to "relaunch" the product internally and are looking for strategic guidance. BUT 🛑 You never follow up with that strategic guidance. In fact, from call to call, you never provide anything other than promises to follow up. You're going to kick the can until you can get answers. The above scenario could be indicative of a CSM who is not performing optimally OR it means that the "best practices" are simply not available and that the work to uncover and collect them is still undone. Here's the bottom line: Part of growing as a CS team means doing the hard work of documenting your knowledge and mining it so that others can use it to empower the work that they do with customers every day. This is true of leadership and individual contributors. Until growing organizations realize this, CSMs will always tailspin in the scenario I described above. Knowledge management is key to growth, enablement, and ultimately scale. #themoreyouknow #customersuccess #leadership

Recently, there has been a lot of discussion on LinkedIn about leadership and management styles, particularly about the importance of being available to team members when they need help. While I see the value in this approach, I believe it only scratches the surface. In fairness, leaders cannot always anticipate the needs of their teams. However, simply asking if someone needs assistance often falls short of meaningful support; it stands the chance of coming across as insincere (e.g. I asked, and they said they didn't need me. Job done). True leadership requires going beyond asking. Here’s why: 🎯 Many times, individual contributors may not fully understand their own needs, especially when they are tackling something new. As a leader, it's crucial to recognize when a task is new and be proactive in providing necessary resources, regardless of whether the person explicitly requests help. 🌠 A more effective approach might sound like this: "I see you're putting a lot of effort into [task name]. I believe these resources could be valuable to you. Let's go through them together whenever you're ready." Simply asking stops short of taking responsibility; taking action demonstrates genuine support. #leadership #themoreyouknow #management

I thought of an interesting analogy the other day: Technology companies are a lot like restaurants. Think about it (and yes, I'm going to make a few generalizations): 🍷 When a new restaurant opens, a combination of the menu (cocktails, wine and food) and location attract customers. 🌟 If the service and food are great, the restaurant will experience some level of longevity along with a solid reputation and loyal customers. 👨🍳 Over time, the head chef keeps true to the vision of the restaurant while meeting customer expectations that the menu will be updated. The restaurants that tend to have stagnant menus, low food quality and poor service stand a strong chance of losing customer interest and ultimately, revenue. Technology companies are often in the same position. If there's a market need and fit, sales will happen and customers will realize value. Over time, if the technology company doesn't update its capabilities, core use cases and demonstrate measurable value, then prospect interest will wane and existing customers will begin to question the relationship. So when compared to a restaurant, how is your technology company doing? How does that pipeline look? #writingonthewall #saas #leadership

I recently joined a call as the "customer" with my assigned CSM and AM from a SaaS provider. Full transparency: we have an active contract and should be using more of this product; the account team knows this too. We've been asking for best practices and more guidance. You'd think our CSM and AM would join these scheduled calls ready to get us using and consuming.  But they're not. By no means do I wish to knock our assigned customer team - they are professional and very knowledgeable. I wonder if they have the time to be proactive in what is clearly a "risky" account situation? It's possible that: 🗣 They need enablement (verbal or playbooks), but their leaders don't have the time to provide it 🌉 The working structure of the team doesn't meet clients where they are (e.g. re-tiering needs to happen along with scale, digital plays and thought leadership) 💻 They don't have the knowledge or access to the resources that would best assist us (e.g. best practices, success stories) My interaction with this vendor is not at all unique. For those of you in post-sales SaaS, you most likely have customer experiences that mirror mine. My experience as a customer is both eye opening and scary - especially if we ultimately churn because we never got the thought leadership and direction that we needed. How does your team structure meet customers where they are? #saas #customersuccess #successplanning

In conversation with a colleague yesterday, we collectively made an interesting observation: Why is it that Sales teams often have multiple layers of specialization and customer success teams don't? If you're an AE, you most likely have someone who: 🎯 Helps to generate leads (BDRs / SDRs) 💻 Discusses technical features and completes custom demos (SE) 📰 Handles the renewal process (AM) Conversely, CSMs need to: 🎯 Identify upsell and cross sell opportunities 🗣 Be a product expert, often with some level of technical expertise 👩🏫 Be a trainer and lead engaging training sessions 👷♀️ Lead onboarding projects like a PM (and possibly more depending on the organization) See where I'm going here?  One of the many reasons why AE's can flourish is because of their ability to focus and specialize in addition to the level of support around them (like enablement). The hallmark of true growth within any organization is when the CS team starts to specialize. Imagine how successful your own CS team can be with the right level of investment. It's better for your teams, and it's better for your customers too. #customerexperience #customersuccess #saas

Years ago, I was laid off from a role I loved. My manager was incredible, and the team I worked with was smart, diverse and talented. When it happened, I was out of town visiting a regional office. I went to the airport early to see if I could get home sooner. I couldn't. All flights were full. While I was at the counter - admittedly crying because I was so sad - someone tapped me on the shoulder. It was an off duty pilot who was also flying to Boston. He asked me what was wrong, and I told him. He said, "You can take my seat." A recent post from one of my connections made me pause. In sharing his experience of being laid off, he talked about the shame we tend to feel. The shame to say it out loud as if we were the cause of it and the odd inclination that some have to "blame" those who experience it. Shortly after the new year, I found myself on the job market after a layoff. I was struggling mentally and emotionally. My connection's post as well as that pilot from years ago brought two things to the forefront of my mind: 1️⃣ There is no shame. Be proud of the work you did. If you do feel sad, feel sad because you miss your team or the fact that you lost a role you loved. 2️⃣ It can be difficult to tell others, but in telling others, you can give your family, friends, and even perfect strangers the permission to support you. If you know someone who has been laid off recently, there are a few things you can do to support them: 💪 Share your networks. Numerous former colleagues reached out to me and offered to make connections. 📣 Offer words of encouragement. Even if it's just a virtual coffee, a quick text message or an email, it can mean a lot to someone who is job seeking. Don't just look at someone's profile. Reach out and check in. 🍞 Share job posts. I had a multitude of people share open roles with me, for which I was very grateful. Job hunting is taxing, and when someone offers to lighten that load, it speaks volumes. Fortunately for me, I have landed in an amazing place. While I consider myself very lucky, I can never forget to pay it forward. We can all do the same. #layoffs #management #people #empathy

At work, we often times manage two sets of expectations: 👩💼 The expectations of our actual job (think: roles and responsibilities) ✨ The unspoken expectations of what others "think" you should be doing Needless to say, it's easier to manage the first set, and the reason is simple: it's defined and shared. The latter is often based on conjecture and on some fundamental level, an inability to communicate. There's often a wide set of "unspoken" expectations out there, including any of the following: --A new leader from an adjacent team makes assumptions about your team and your role --The departure of colleagues (either planned or unplanned) and the question of whose role will "fill in" the gaps --The "who" of who's communicating or completing a task is (wait for it) you While it can be challenging to manage unspoken expectations, there are a few things that you can do to uncover them: 1️⃣ Ask for clarity 2️⃣ Ask about what organizational changes imply - for yourself and for other teams (e.g. this person used to be responsible for x. who is responsible for that now?) 3️⃣ As expectations are uncovered, ask how these align with your current role and whether your performance evaluation should now include these new areas (e.g. new responsibility or MBO) In short, asking the above questions can help to define out how you're truly being evaluated. While it may be somewhat uncomfortable to ask, the fact is that you need to. It's the unspoken impressions and assumptions that can negatively affect us, and this is particularly more acute in fully remote environments. #management #people #layoffs

Last week I had lunch with a colleague where we discussed my love for all things interior design and architecture. I shared that my favorite design movement is the Bauhaus. Reflecting on the conversation, I realized something: the Bauhaus design approach offers an incredible analogy to the effectiveness (or lack thereof) of different leadership styles. Here’s how: The Bauhaus was an attempt to unify individual artistic vision with mass production while enabling individual artists to collaborate. This is in contrast to Frank Lloyd Wright and the Unsonian approach to design. Wright’s vision of designing in harmony with humanity and the environment (definitely resonates as a solid design philosophy, don't get me wrong) but there’s a distinct difference: –The Bauhaus emphasized a collaborative design process  –Lloyd’s process put him (and any other lead architect) at the center of the design Key to the success of both approaches is clear, consistent communication and a high level of trust. In traditional work environments (think non-creative), how does this often pan out? Sometimes great, but not always. To echo my post a few weeks ago about defined process: If the approach for getting things done is left undefined - whether there’s a leader who cannot effectively communicate the “how” or because of assumptions that are made about the people “doing” the work (e.g. they’ll figure it out / they know without my telling them), something will definitely go wrong every single time. So while the principle may be sound, the approach can contain cracks that are difficult to fill. Just ask any repair person working on a Frank Lloyd designed roof. #leadership #saas #process #layoffs

While browsing LinkedIn recently, I scrolled past a job title that made me pause: "Strategic Customer Success Manager." This begs the question: What does this imply for the other Customer Success Managers (CSMs) on the team? Does this insinuate that they lack strategic prowess or operate differently? CS practitioners may be overlooking a crucial point. While pooled, scaled, and digital approaches have their merits, any model must incorporate a strategic component. Whether working directly with clients or working behind the scenes, strategic thinking should underpin every action for a CSM. However, explicitly including "strategic" in the job title, thereby making it visible to customers, could carry negative connotations. As a customer, I might instinctively question the necessity for such a qualifier. Am I wrong here? #customersuccess #saas #management