Digital technologies are disrupting all economic sectors, wedging regional firms into competing low- or high innovation trajectories. The uneven and asynchronic proliferation of digital technologies between firms and between regions are creating differentiated demands for high and low skill workers; in some cases upskilling workers and increasing wages when successfully coupling with digital technologies, and in other cases deskilling, suppressing wage increases and substituting labour. In this case study we examine wood product companies in the Canadian Atlantic provinces, digital technology investments and their digital skills assessment of workers. Our findings reveal bifurcated trajectories in the use of digital technologies and skills between younger, smaller wood product companies and longer-established incumbents. Younger companies were more likely to invest in advanced digital technologies, invest more in workers and pay higher wages and develop new products and markets (bioenergy, medtech, advanced composites). While this suggests local governments would privilege higher technology-skill trajectories, market power and policy capture tended to preserve the status quo.