I engage with 20-25 sales leaders every week, gaining invaluable insights from them and often sharing my own observations and perspectives.
The world of sales has transformed dramatically over the past decade — from field reps to the SDR model to the advent of Rev Ops. Drawing from my exchanges with prospects, my network, and even our clients, here are the most fundamental gaps I’ve observed:
- Backward Modeling in Sales Strategy
The issue is as old as sales itself, and it's surprising how prevalent it still is. Instead of asking "who can we serve" and considering the Total Addressable Market (TAM) multiplied by conversion rates, many sales leaders start with (or are assigned) an arbitrary sales target and then reverse-engineer from there. However, a great sales organization knows its customers intimately, including the number of accounts and roles within them they can best serve. This knowledge acts as a North Star, guiding the strategy, setting expectations, and forming the backbone of the financial plan. Confidence in this data fosters a culture of collaboration and keeps the team motivated.
- A Dip in Deliverability Knowledge
Despite the persistence of outbound techniques, understanding of deliverability is at an all-time low. Automation is essential for sophisticated, repeatable processes. The number of touches needed to educate, engage, and convert leads is far too high for manual efforts alone. Tools like Salesloft, Outreach, or Hubspot are handed to reps with a simple directive to 'go'. While some may opt for highly personalized campaigns yielding a few meetings, this approach often falls short of meeting their quotas. Others resort to 'spray and pray', damaging domain reputations and hitting nothing but spam filters. This circles back to my first point — by starting with a clear understanding of whom you can serve, you can segment your team's efforts, setting realistic volume expectations and providing targeted content recommendations. The keeps integrity in your outbound, and campaigns may be automated, the volume is humanized, and is not reckless to the domain.
- The Best Sales Folk are Math Folk.
The best sales leaders I’ve encountered possess math skills and creative skills. Think about it - we need the math to set the right expectations for the funnel and team, but also need the creativity to engage and communicate with a vast range of people. They’re reviewing past trends to calculate probabilities and formulating quotas that are not only ambitious but also statistical realities. This is the most fun part our job here at AK Operations - taking an arbitrary goal and then running the numbers of what it will take to get it done. Or contrary - we will build a model of what we can expect (typically a conservative and reach goal) based on the TAM we serve best and convert well in the pipeline. I never want to discredit the impact of a charming sales leader who can motivate their team and build compelling relationships with their prospects - but you need both - the savviness of a mathematically driven sales leader is where it’s at IMHO.
- The Misguided Push for Omni-channel
I'm a staunch advocate for humanizing sales and have seen significant improvements when integrating calls, LinkedIn, and digital marketing. However, I’ve also seen a rise in sales rep burnout due to poor rollout and perception as an added burden. Proper enablement is critical to close the loop on marketing spend like this. A disengaged rep is a liability to your strategy, team, and sales plan - so please, introduce omni-channel initiatives thoughtfully, with clear expectations. It's not just about the number of touchpoints, but about making each interaction count.
For example, we've designed unique touch points for different roles we target. Our reps won't reach out cold; they engage only after we've warmed up the account. Our enterprise rollout includes:
- LinkedIn: Engage with all buying team members post-meeting booking, follow up after the meeting to introduce yourself, and reach out to hard-to-get titles who have engaged with your emails.
- Calls: Calls are no longer cold and arbitrary; they're strategic and prioritized based on digital engagement, amplifying their impact and connect rates (typically 10%!). It's our job to enable reps to use their time effectively, such as by prompting calls when there's engagement from ideal customer profile (ICP) accounts or new website activity.
- Digital Marketing: We can't tackle all aspects of digital marketing at once without diluting our efforts. Instead, focus on retargeting key accounts and re-engaging past prospects to maximize impact. Then roll out additional cold campaigns once you have a steady hold on your top titles and industries, top engaging marketing assets or demo requests, and most likely to convert follow-up strategies. The conversion on digital is just step one - the ROI in digital is 100% in the follow-up to get it on the books.
TL;DR: By understanding who we serve and aligning our strategies to meet their needs, we’re not only building a plan you can feel good about, but you’re also doing it with stewardship in mind to truly solve the problems of our customers. That fundamental shift brings integrity to all the other gaps I mentioned too - the desperation of spray / pray and its pending deliverability issues, the expensive misses of digital omnichannel rollouts, and ultimately rep burnout and missed numbers. We can create a sales model that is both effective and sustainable if we can get these four things dialed in.
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