Being in sales, we experience challenges on a daily basis. One of the bigger frustrations is having a great quarter or year and then seeing the dial goes back to zero, knowing you need to start all over again. It’s what we all sign up for, but that doesn’t make it any easier of a pill to swallow. As a sales leader, one of the biggest challenges can be motivating reps to maintain consistency. Keeping reps motivated to successfully climb the mountain each quarter is not a one size fits all approach. For some reps, it’s providing growth and development opportunities that keep them driving, for others it’s SPIFs and recognition that helps them get where they need to be. Finding a way to effectively manage your time can be another big frustration. At times, the sheer number of responsibilities on our plate can feel overwhelming. It’s hard when everyone seems to need something from you and there aren't enough hours in the day. I’ve found that it’s important to be as highly organized as possible, prioritize tasks, learn your productivity patterns, block out calendars to complete important activities and schedule breaks to refresh.

People's definition of 'hard skills' may differ depending on where they work, what the sales organization makeup is, and what product/platform they are selling. In my experience, the 'gold standard' sales leaders have a few attributes in common when it comes to 'hard skills'. For instance all seem to possess the ability to be dangerous with their technical skills, and business skills - similar to what we would may say about someone outside of work: they are book smart, and street smart. Strong leaders can keep up with the IT and Platform executives, but can also 'wow' prospects and partners with their ability to tell an effective story. Also, they appear to be educated and comfortable with the 'best of breed' platforms and applications, ensuring they stay on topic of the latest in tech. Finally, the strongest leaders I have worked alongside all have deep analytical skills that are super impactful to the sales organization including data analysis, research, creativity in problem solving, and are wonderful communicators.

Coming into an organization as the first sales hire puts a lot of responsibility on your shoulders. You are basically in charge of proving the validity of this function within the company. There are a few things that I would consider and act on in this position: Start with the short term. As a first hire in a sales organization, you are required to deliver results that have a very immediate impact that meets the business needs. This means focusing on some low-hanging fruits in order to deliver results within a short time frame. Build a framework. As a first hire within the team, you should make sure you document your work, and create clear guidelines and processes, with the expectation of adding additional members to the team in the future. This will ensure a smooth expansion of the team while positioning you as a thought leader and a pivotal member of this function. Go beyond your scope. As a junior sales hire, never underestimate the power of tenacity. I always invite my team members to push the boundaries and look for additional scope and responsibilities whenever they feel capable. This is a very strong signal that you are willing to take on more, and when management will face a new task at hand, they will know they can count on you.

One word: outcomes. Sales enablement should (and needs to be) tightly aligned to business objectives & desired outcomes of the business/sales organization. When you tie learning programs to tangible outcomes & KPIs, you get more accurate success measures. This translates to happy learners and happy business units: win-win.

Rep ramp-up time in my opinion is something that I've seen companies completely overlook. Given the boom tech has been on over the last decade many companies have skipped tracking key fundamentals from the moment you decide to hire the rep to the moment they hit quota due to them smashing their numbers. A key example of this is certifications around product knowledge. Assessing an AE's product knowledge and understanding of the enterprise software solution they are selling is key to this period. This can be achieved through role-playing, pitch certification, standing and delivering on specific product value props, etc. We've veered away from rigorous sales onboarding training in exchange for throwing them in the deep end quicker hoping they'll hit quota, succeed, and contribute to the company without laying the proper foundation.

Sponsors are critical for career progression. When you think about the best persons to lean on for sponsorship, you should be thinking about someone who is already bought into you and would endorse you to others within the business. You want to also ensure that this person is well connected and has a "voice at the table" that you don't have a "seat" at yet. Then, you need to ask that person for their support. Most importantly, you then need to create value and as mentioned in another response, ensure the things you are working on and focused on to create value align with what is important to the business and will create impact at scale. 

So much of the sales KPI tracking has been automated (# meetings, Pipeline generated, funnel progression) so I find the manual ones more difficult to track, but move the needle the most. ie: how many on-sites did a rep conduct this quarter? It's a manual process for reps to log into a CRM and update a meeting field as "in person" and often gets over looked in an organization. There is no substitute for in person meetings. Another example that's difficult to track things like how many new business units or contacts from other business units you broke into in a month, quarter, or year.

Our top reps excel at spotting potential opportunities. Since we're focused on run-rate tactical deals in the form of additional license, new initiatives, and pilots, our main stakeholders are typically at the VP level or below. The key here is mastering the art of tailoring conversations - distinguishing between "above the line" and "below the line" discussions ensures that our messaging aligns with the audience. In larger enterprises, industry trends and company direction are often widely available. It's crucial to delve into these trends, gaining a deep understanding of industry challenges and directions. This forms the basis for crafting a unique perspective that resonates not only with the business but also its key players. Once everyone's on the same page and the problem is crystal clear, we can then propose a forward-thinking solution that drives them towards their desired outcomes. What sets this approach apart is its emphasis on discovery. Rather than leading with a product pitch, we invest time in understanding the company's priorities. This makes our interactions much more aligned with the client's needs, creating a more genuine and less "sales-y" experience. This method ensures that our solutions aren't just one-size-fits-all, but tailored to fit the precise needs of each client we engage with.

If an account executive is sharing feedback (positive or negative!), here are a few questions you can ask to decide how to incorporate it. 1. Is the feedback specific? To act on feedback, we have to have enough information to properly diagnose the cause. If an AE shares that an account was unqualified, did they share the name of the account and the particular reasoning? 2. Do we know what led to the feedback? To act on feedback, you have to know what to change. Identify the specific behavior or process that led to the feedback. In this case, perhaps there was a qualification question that wasn’t asked or we had incorrect data in the CRM about the account. Different causes require different solutions and we shouldn’t assume the cause. 3. Is this an individual occurrence or a trend? Ask if they have any additional examples for the feedback or even recent counterexamples. Scoping the occurrence of the feedback will help you figure out if you need to work with single individuals or change an overall process. Don’t treat feedback as global unless you have shown a sufficient sample size. Once you have gotten the above information, you can decide how to implement a change (and if a change is worth implementing). If the feedback seems to be coming from a one-off situation, you may want to approach at the individual level. If the feedback seems to point towards a larger trend, you may want to design an experiment or A/B test to see if the suggested changes work. Lastly, make sure to proactively request feedback from the AE team. Their input is particularly valuable for (1) deciding how to prioritize account books and (2) refining your Ideal Customer Profile and even identify new use cases. 

I stole the idea of “WGLL” from Kevin Dorsey, who works across his leadership structure in sales teams to be maniacally focused on what good looks like, and work backwards from there. As such, I’ve rooted our metrics in support of WGLL - not from the perspective of “Amy & Bobby are the best, let’s have everyone do what they’re doing!”, but rather in using WGLL activities across my sales leaders to understand specific wins from the sales funnel and the supported customer experience to drive those metrics of success. For an example: we found that Amy is delivering a lot of value in the on-sites she’s running in her territory, let’s equip the team with her model (How far out she schedules, targeted personas, decks + sequences to set the meeting) and then hold them accountable to a number that Amy has driven to: 2 on-site meetings per month. Bobby is doing fantastic work top of funnel, and so we’ll capture what personas he’s engaging, what content and sequences he’s sharing, and communicate that as the KPI to the rest of the team.