As the new sales manager for a B2B SaaS company that is starting to scale with 40 people, your first month and first quarter are critical for laying the groundwork for future success. Here's what you should aim to do in each timeframe: First Month: 1. Understand the Business: * Gain a deep understanding of the company's products, services, target market, value proposition, and competitive landscape. 2. Assess Current Sales Processes: * Evaluate existing sales processes, tools, and workflows to identify strengths, weaknesses, and areas for improvement. * Review sales metrics, performance data, and historical trends to identify patterns and insights. 3. Build Relationships: * Get to know your sales team members individually, understand their strengths, weaknesses, and motivations. * Develop rapport with cross-functional teams, including marketing, product, customer success, and operations. 4. Set Expectations: * Clearly communicate your vision, goals, and expectations for the sales team. * Align sales objectives with broader company goals and priorities. 5. Identify Quick Wins: * Identify low-hanging fruit and quick-win opportunities to boost morale and generate early momentum. * Focus on addressing any immediate challenges or bottlenecks that may be hindering sales performance. First Quarter: 6. Develop a Sales Strategy: * Develop a comprehensive sales strategy that aligns with the company's growth objectives and market opportunities. * Define target customer segments, ideal customer profiles, and go-to-market strategies. 7. Optimize Sales Processes: * Streamline and optimize sales processes to improve efficiency, effectiveness, and scalability. * Implement standardized workflows, sales cadences, and best practices. 8. Provide Training and Development: * Implement a structured onboarding program for new hires and provide ongoing training and development opportunities for the sales team. * Focus on building sales skills, product knowledge, objection handling, and negotiation techniques. 9. Implement Sales Technology: * Evaluate and implement sales technology tools and platforms to support sales operations, enablement, and analytics. * Implement a CRM system to track leads, opportunities, and customer interactions. 10. Set Performance Metrics: * Define key performance indicators (KPIs) and metrics to track sales performance, such as conversion rates, pipeline velocity, and quota attainment. * Implement regular performance reviews and coaching sessions to provide feedback and support to the sales team. 11. Foster a Culture of Accountability: * Foster a culture of accountability, collaboration, and continuous improvement within the sales team. * Celebrate successes, recognize top performers, and address underperformance proactively. 12. Align with Leadership: * Maintain open communication and alignment with executive leadership, providing regular updates on sales performance, initiatives, and challenges. * Seek input and guidance from leadership to ensure alignment with company goals and priorities. By focusing on these key initiatives in your first month and first quarter as a sales manager, you can establish a strong foundation for sales success, drive growth, and position the company for long-term scalability and profitability. ChatGPT can make mistakes. Consider checking important information.

This one’s easy! In sales, your performance metrics are your best evidence. Start with your revenue numbers—they’re the clearest indicator of success. Beyond that, track and showcase your quarter-over-quarter (QoQ) improvements in metrics like close ratio, deal size, or pipeline growth. For example, demonstrating consistent improvement in your ability to close deals is a strong justification for a salary increase. Tracking your own metrics not only helps you improve as a sales professional but also shows leadership you’re thinking strategically and providing valuable insights to the business. Thus making the business ant to invest in you further.

My two favorite technique to use when you believe a client may not be telling you the whole story is: 1) Humbling disclaimer - you can disarm a prospect who may be withholding information by humanizing the conversation and providing a humorous, self-deprecating "humbling disclaimer". This could sound like, “I’m sorry, but I must need another cup of coffee, because I just don’t get it, can you help me understand why that may be the case?” 2) Suggestive discovery - normalize the situation or state, and then asking a question informed by your perspective to probe deeper to get to the truth. That could sound like, “Got it, typically I’ve observed when other clients…it’s because of…to what extent would you say that is what is going on here?” With those two tactics, you can usually get to the truth of what may be happening.

With most of these questions, there isn't a one size fits all. Consider things like: * Company stage * Growth objectives * GTM strategy * Customer segmentation * Self serve vs. sales led * Compensation modeling AI has, of course, been a hot topic lately, begging the question of which roles will become obsolete. Personally, I think there will always need to be a human element. This AMA is a great example. If you wanted these answers you could find a generic response in Chat GPT vs. reading my response, but you are looking for the human experience aspect that ideally will provide you with more value. Below is a brief rundown of how I'd think through my org structure coming in at an earlier stage business. It's less about the actual title of the role and more about the function itself: * Inbound vs. outbound * Marketing * SDR * Partner/Channel * Customer acquisition * AEs * Customer retention * Onboarding Specialists * Customer Success/Account Management * Customer expansion * AE * Customer Success/Account Management * Customer reporting * Revenue Operations * Customer value * Sales Engineers * Solution Consultants * Leadership * Revenue * Sales * Customer Success * Revenue Operations Are all of these roles needed to get started? No. Figure out where you can create overlap in your roles by working backward on your bottoms up modeling for your revenue targets and determine how many people to need in order to achieve those goals. From here, you can uplevel the structuring into categories: * Functional: Think specialists vs. generalists. Core vs. overlay * Geographic: Location specific * Market Based: Industry/vertical specific * Product Sales: For larger organizations, this can be based on product SKU, bundle, etc. to drive certain revenue engines of the business

* A clear perspective backed by data and customer examples * Brevity while still ensuring substance * Creativity in finding solutions that may not align perfectly to only the thing you had in mind. I screwed up both these things on two separate occasions in highly visible roles where the cost to me (and my sanity on the days that followed) wasn't small. I didn't let the work nor my commitment to finding a suitable resolution fade into the background. Instead I doubled down my commitment to find creative solutions, digging more deeply into the data and customers and using 1:1s and quick actions to show my commitment to seeing solutions through.

Top performers can distort KPIs that you want to roll across your team. On one hand, sales professionals are able to achieve excellence because they do the right things consistently “We are what we repeatedly do. Excellence, then, is not an act but a habit.”. For a salesperson like this, we will strive to understand how those habits inform their success, and which of those therefore should be transmutable across the team to drive success for others. On the other hand — this is not popular to say - some of your best sellers are simply far more talented. They will not need the same amount of “at bats” that you’re measuring throughout your sales funnel as the sales reps who are a standard deviation or two less talented. Do not build KPIs off of these individuals.

I alluded to this in an earlier question, there will also be those KPIs that come as "standard" to the sales job. How many calls did you have in a week, how many discovery calls vs demo calls, etc. However, what I pay most attention to is what KPIs do top sellers consistently hit? Do they do more in-person meetings? Do they leverage Executives more? How often do they expand into another business unit in an org? I map out KPIs based on top performers and hold reps accountable to that activity.

Integrating effective discovery into your presentation and demonstration process is the differentiator between consistently winning and struggling to close deals. Value-based selling demands that discovery is seamlessly woven throughout your engagement with prospects. When executed properly, this approach enables you to: 1. Deeply understand the customer's pain points and their broader implications. 2. Connect these pain points to relevant, successful customer stories. 3. Clearly outline tactical capabilities that address these pain points and confirm alignment with the prospect's needs. 4. Guide the prospect towards "value day" — the moment when they acknowledge the solution has resolved their challenge. By focusing on discovery, you control two critical outcomes: * Validation of the Customer’s Pain: Confirm the pain is significant, and that the prospect is committed to addressing it. * Demonstration of Value: Map pain directly to value, ensuring a tailored demonstration that resonates. Avoid generic, one-size-fits-all demonstrations. Instead, focus your demo on solving the customer’s most urgent pain points—the issues that generated genuine engagement during discovery. Key Execution Tips: 1. Customize Your Demo: Avoid "canned" demos—these are for marketing, not high-impact sales. Start with the pain point that resonated most with your prospect and build from there. 2. Demonstrate Pain-to-Value Continuously: Throughout the demo, take the opportunity to ask, "Can you see how [our solution] helps you overcome [specific pain point] we've discussed?" This ongoing dialogue builds clarity and reinforces alignment. 3. Drive Confirmation and Momentum: Repeat this process at least three times. It reinforces the connection between pain and solution, drives momentum, and elevates the prospect's confidence in you as their preferred vendor. Remember, winning is about understanding and empathizing with the customer's challenges, and proving your ability to solve them effectively.

Re-evaluating KPIs on a regular basis is a healthy practice for your company. Just because it worked this year, doesn't mean those same motions will work next. For instance, in year's past, you may have been okay working with a Business Head to justify budget. Nowadays, CFO's are scrutinizing expenses more than ever, expecting to see the R in ROI. If you are not involving them early, your success rate is likely suffering. You'll want to evaluate the attributes making up your wins vs the deals you lose, before determining what to use moving forward. It could be access to power, Executive alignment, departments involved, breadth of solution to differentiate from competition, on-sites delivered, problems you're solving, or length of sales cycle. Identify your trends and set those as your targets. Then make sure you have a simply process to track the data and hold your sellers accountable.

Having been someone who has expanded an office in a new region I can certainly empathize with anyone who is in this situation at the moment and I totally understand the hard work that goes in to getting a new market off the ground and eventually hitting goals. In this scenario I would recommend taking the time to understand the cultural buying norms of the new market and not assuming this new market will look immediately like your top performing markets. It takes time to understand a new market and the buying intent of customers. Set yourself KPI goals based on shorter time periods and make sure you review the success of these goals on a regular basis. Be willing to switch them up when you see any trends forming. Finally, don't be afraid to admit when things haven't worked. Just be prepared to change it with a strategy that makes more sense for the market you are in and be able to defend the strategy shift backed by intel you have gathered while selling in the new market.