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.

Another great question and one that will certainly differ from executive to executive. However, in my experience some of the top intangibles for the top performers I have seen include: - Confidence and a winning personality. Now, I don't want to confuse 'confidence' with 'ego'...to have 'confidence' is to believe in yourself and your own abilities. 'Ego' on the other hand operates out of self interest, and 'lone wolves' do NOT work in today's high performing sales teams. - Being a 'consultant' and expert in your industry. Now, I don't expect every seller on the team to be able to lead a 'Ted Talk', but do your homework with your top accounts - understand the top challenges and opportunities in the industry they are facing. Read up on the company and understand what they are trying to achieve in their current environment, and get to know the motivation for your contact - what are they trying to achieve and how can they be your champion? - Customer focus and appreciation. The sales teams I want to be most associated with are ones that realize the customer relationship truly begins once the deal has closed. Too often sellers are off to the next chance to retire quota, and they lose sight of the long term benefits of being customer centric. Think 'seed and grow', not 'sell and go'. Also, being responsive and available to your accounts, whether 'prospects' or 'customers' is also key. People will remember those who respond in a timely fashion to any outreach from their accounts - goes back to the earlier point of differentiating yourself in small, but significant ways, and helps grow customer confidence and retention.

Be transparent and share the “why”: Each SDR should be able to articulate the purpose of their role, the rationale behind their goals, and the methodology used to calculate key performance indicators (KPIs). While many teams have robust processes to determine these factors, they often fail to provide transparency to their teams. When metrics are perceived as being dictated without explanation or “handed down”, they become less motivating. Encourage individuality- Find areas where SDRs can flex their creativity, contribute to experiments, and express their opinions. When you go overboard with processes on an SDR team, it takes away the joy from the work and lowers the possibility of discovering impactful ideas. Create a team that defaults to collaboration and praises readily- While a slack channel, shout-out specific application, or kudos google form can be well intentioned, they often go underutilized. We know that if our team has downtime, they are probably using it to update Salesforce. Make giving praise part of an essential process that is already done!

The answer to this question depends on the sales leader (i.e. me vs someone else), the product that the rep is selling, the stage of the business, etc. The list goes on. I personally am always looking for candidates who have these two attributes: 1. Innate curiosity 2. Persuasiveness The first is (hopefully) obviously critical. The more curious the rep, the better they should be at discovery. The better they are at discovery, the more time you can spend helping them execute the back half of their deals. The second is also hopefully obvious. I know plenty of reps who excel in sales through discipline and structure, but I'd take a rep who is also persuasive (on top of those things) any day of the week.

I am a firm believer of meritocracy. So when it comes to pay raise especially in sales roles it should be very black and white for a sales rep to determine when would they qualify for a pay raise. It should be very easy for sales people to chart out their salary hikes based on their performance. The more consistent you are in delivering and over achieving your targets, the faster you should get to your pay raise. Needless to say, that there is no compromise when it comes to ethics and integrity when you are achieveing your targets.

I'll be honest, I've been in the Sales Enablement industry for a while and this is something that takes so much time to master and has so much nuance depending on your organization's structure. Here are some tactics I use that have helped me get 80+ people in my last annual strategy review. It boils down to these three things: 1. What you did: I LOVE quarterly business reviews. Now let's be honest, I HATE writing them, but they are very effective in getting engagement. The two questions you want to ask here are: 1) Who's the audience(s) I'm trying to activate? 2) What information are they looking for that would gauge proof of investment return and guidance? For me, I typically stick to a common format: * Divide the document by program * In each program, share objectives that you've set at the beginning of the quarter/year, what major projects were activated to address these, achievements, key insights and feedback, and next steps (how you're building on it, how you're pivoting away from it, and what you need help with by cross-functional department) * Tag specific people you know that would be interested in areas that pertain to them * Create a read-through event and ask folks to add comments and tag others who would be interested * Leave room for discussion of key themes at the end 2. What you're going to do: In addition to the quarterly business review, I do an annual review that considers any strategic plans for our key audiences, mostly this will be Sales Leadership's north stars. If you don't have these plans, go off of the business goals and vision for the year (team restructuring, market expansion, change in target audiences, etc). Here's my typical format: * Goals and objectives from the previous year and share loosely what your team achieved * Key insights that are going to guide you in the new year - changes in team habits, cross-functional partnerships, industry changes * Identifying those business objectives and the strategies (the direction, not the roads) you'll be taking to get address them - focus on why you are doing this from an enablement professional perspective * Divide the following sections by quarter, refer back to the objectives and strategies and key initiatives. Make sure to call out dependencies, financial/cross-functional resources needed, priority levels. This is a great place to be clear about who you need these from and ask for DRI's from their teams through comments * Give gratitude to your partners for making this happen and look forward to the collaboration needed to make this happen 3. How it's doing: These are weekly or monthly updates on those objectives and key initiatives. Share your current state in achieving those objectives and the deliverable progress for key initiatives. I also include some key themes and insights that we see in the data and feedback we hear from reps. This is also a great place to share what you're hearing from the industry/enablement world and how you plan to integrate them. All of these have really jumpstarted interest in our programs by being clear on guidance for why and how your partners can help will get it going. Make sure that you secure clear partners, project owners, and recurring times set to meet with them. Hope these help!

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. 

To effectively manage complex deal structures and negotiations, it boils down to a deep understanding of the customer's objectives and their timeline for achieving them, and most importantly which internal resources they will need to progress the opportunity. Once we've identified the "when," the next critical step is crafting a mutual close plan that outlines the roles of both internal and external stakeholders. However, it's imperative not to develop this plan in isolation. Every facet of our business must be in sync and fully committed to executing this mapped-out strategy. Without explicit agreement and a shared commitment to the timeline, progress can feel like an uphill battle. If it becomes apparent that the customer is not fully aligned with our mutual plan, it's a clear sign that there's a misalignment somewhere in the buying cycle. In such cases, I advocate for taking a step back, seeking realignment, and securing a renewed commitment from the business before moving forward. We understand that priorities shift, personnel changes occur, and budgets may be reassigned. Thus, it's essential to maintain a rigorous qualification process at every stage, ensuring a clear outcome and timeline. While this approach may seem deliberate, it ultimately accelerates the process in the latter stages of the sales cycle. By diligently bringing in the right people at the right time, we maximize our chances of success and create a smoother path to closing the deal.

I don’t believe there’s a single "right" career path for a sales professional. Sales is an incredible foundation that can lead to countless opportunities because the skills are universally valuable. Whether you’re pitching investors as a founder or advocating for an internal business initiative, you’re always selling—yourself, your ideas, your vision, or your work. Traditionally, Sales careers may start as an SDR, progress to AE, Mid-Market AE, Enterprise AE, and eventually to Client partner or Senior Relationship Manager. Alternatively, you might take the leadership path, from sales manager and graduate to senior leadership roles. Ultimately, your path should align with your strengths and what gets you excited every morning.

By conducting a bi-annual survey and constantly checking in with them regularly. Attending their weekly meetings is a great start to becoming part of their team and really begin to understand what they need and how you can provide it to them. It is also a great idea quarterly to interview about 15-20 sellers to stay connected to their requirements.